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Chemical Structure| 538-51-2
Chemical Structure| 538-51-2
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CAS No. :538-51-2 MDL No. :MFCD00003027
Formula : C13H11N Boiling Point : -
Linear Structure Formula :- InChI Key :DSGKWFGEUBCEIE-UHFFFAOYSA-N
M.W : 181.23 Pubchem ID :79668
Synonyms :

Safety of [ 538-51-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 538-51-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 538-51-2 ]

[ 538-51-2 ] Synthesis Path-Downstream   1~85

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YieldReaction ConditionsOperation in experiment
96% With tris(bipyridine)ruthenium(II) dichloride hexahydrate In acetonitrile at 25℃; for 1.5h; Irradiation; Green chemistry;
96% With carbon dioxide; DBN; Eosin Y In dimethyl sulfoxide at 25 - 30℃; for 48h; Irradiation;
95% With MS3 Angstroem; oxygen; sodium acetate In N,N-dimethyl-formamide at 80℃; for 14h;
94% With oxygen In para-xylene at 120℃; for 5h;
91% With manganese(IV) oxide; molecular sieve In hexane for 1h; Heating;
86% With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene at 20℃; for 0.00833333h; Inert atmosphere;
84% With potassium carbonate; 1-(tert-butylperoxy)-1,2-benziodoxol-3(1H)-one In benzene for 25h; Ambient temperature;
82% With iodosylbenzene In dichloromethane for 24h; Ambient temperature;
80% With dodecacarbonyl-triangulo-triruthenium; iodomesitylene; N,N'-1,2-tetrakis(4-fluorophenyl)ethane-1,2-diimine; caesium carbonate In chlorobenzene at 150℃; for 16h; Inert atmosphere; Sealed tube;
79% With tert.-butylhydroperoxide In benzene at 60℃;
73% With dichloro(benzene)ruthenium(II) dimer; hexamethylenetetramine In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux; Green chemistry;
68% With rhodium(III) chloride hydrate; C13H19N4(1+)*Br(1-) In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere; 4.2. General procedure for dehydrogenation of amine General procedure: RuCl3nH2O (0.5 mol %), HMTA-Bz (1 mol %), amine (0.25 ml)and dry toluene (1.0 ml) were placed in a Schlenk tube. The reactionmixture was stirred under open condition to nitrogen andrefluxed for 24 h. After completion of the reaction all toluene wereevaporated under vacuo, the oxidized products were isolated fromcrude mixture with the help of column chromatography using hexane/EtOAc as eluent. The formation of products was confirmed bycomparing the 1H NMR data with literature reports.
65% With 4-tert-Butylcatechol; oxygen; potassium carbonate In chloroform; water at 35℃; for 16h;
44% With tert.-butylhydroperoxide; 1.8Co(2+)*1.2Mn(2+)*2C9H3O6(3-)*3H2O at 80℃; for 24h;
41% With [RuCl(ppy)(tpy)][PF6]; oxygen; potassium carbonate In d(4)-methanol for 24h; Reflux;
21% With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; oxygen In acetonitrile at 35℃; Molecular sieve; Irradiation;
13.1% With potassium <i>tert</i>-butylate In toluene at 40℃; for 2h;
With potassium permanganate; acetone
95 % Spectr. With 4 A molecular sieve; 4-methylmorpholine N-oxide In acetonitrile for 6h; Ambient temperature;
With oxygen In various solvent(s) at 99.85℃; for 15h;
99 % Spectr. With air; 2,6-dimethoxy-p-quinone In toluene at 110℃; for 24h;
With oxygen In various solvent(s) at 99.84℃; for 15h;
18 %Chromat. With oxygen In toluene at 100℃; for 24h;
96 %Spectr. With graphite-supported gold nanoparticles; oxygen In toluene at 110℃; for 24h;
90 %Chromat. With oxygen In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h;
With iron oxide surrounded by nitrogen doped graphene shell immobilized on carbon support In n-heptane at 100℃; for 12h; Autoclave;
55 %Chromat. With oxygen; potassium carbonate In neat (no solvent) at 100℃; for 8h; Schlenk technique;
With oxygen In neat (no solvent) at 109.84℃; chemoselective reaction;
With oxygen In neat (no solvent) at 119.84℃; for 2h; 2.3. Catalytic activity General procedure: The catalytic performance of the prepared samples was investigated for the oxidation of benzylamine using an O2 balloon under solvent-free conditions. In a typical experiment, 0.2 mmol of substrate and 100 mg of catalyst were taken into a 10 mL round bottom flask and stirred magnetically at required temperature for appropriate time. After completion of the reaction, the catalyst was separated from reaction mixture by centrifugation. The products were confirmed by GC-MS equipped with a DB-5 capillary column and a flame ionization detector (FID). Samples were taken periodically during the reaction and analyzed by GC equipped with BP-20 (wax) capillary column and a FID.
61 %Chromat. With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen In N,N-dimethyl-formamide for 16h; General procedure for the dehydrogenation of N-heterocyclic amines General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.
37 %Spectr. With C38H61N5OsP2 In para-xylene at 140℃; for 48h; Schlenk technique;
With potassium permanganate; acetone
With oxygen In acetonitrile at 20℃; for 20h; Irradiation;
With manganese(II) bromide; dipotassium peroxodisulfate In acetonitrile at 100℃; for 24h;
96.8 %Chromat. With cobalt nanocrystals stabilized by nitrogen-doped graphitized carbon; air In methanol at 50℃; for 12h;
With bismuth subcarbonate; oxygen In acetonitrile at 25℃; for 6h; Irradiation; Sealed tube; Autoclave; Green chemistry; 2.4. Photocatalytic oxidative coupling process of amines General procedure: All photocatalytic experiments are performed in a 120 mL autoclaveequipped with a glass window and magnetic stirring. A typicalprocedure for the oxidative coupling of benzylamine is asfollows: 0.1 g of benzylamine, 0.025 g of flower-like Bi2O2CO3 catalystand 10 mL of CH3CN solvent were charged into the reactor,and the atmosphere inside was replaced with oxygen for threetimes after the reactor was sealed. Then, pure oxygen was chargedto 0.3 MPa at room temperature. Subsequently, the mixed solutionwas irradiated through the window of autoclave with a Xe lamp,and then was kept for 6 h under stirring. After reaction, the excessgas was purged. The mixture was transferred into a 100 mL volumetricflask, in which the reactor was washed with ethanol for3-5 times in order to transfer completely. The obtained productswere analyzed with internal standard technique by GC with aflame ionization detector (all products were determined on GC-MS with an Agilent 6890N GC/5973 MS detector).
With potassium <i>tert</i>-butylate; oxygen In tetrahydrofuran at 130℃; for 16h;
With 2C32H16O4(2-)*3Zn(2+)*2HO(1-)*3C5H11NO; oxygen In N,N-dimethyl-formamide for 27h; Irradiation; Sealed tube; Green chemistry;
With water In acetonitrile at 25℃; for 16h; Autoclave; Inert atmosphere; Irradiation; Green chemistry;
With C66H42N12 In dichloromethane at 20℃; for 3h; UV-irradiation;

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YieldReaction ConditionsOperation in experiment
beim Schmelzen;
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YieldReaction ConditionsOperation in experiment
at 170℃; im Autoklaven;
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  • 1-anilino-1,2-diphenyl-hexan-3-one [ No CAS ]
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  • [ 108-59-8 ]
  • [ 164172-51-4 ]
YieldReaction ConditionsOperation in experiment
95% With L-glutamic acid In ethanol at 20℃; for 5h; Procedure foramino acid catalyzed two-componentMannich reaction General procedure: In a 25ml single-neck round bottomed flask, the solutionof imine (0.5mM), ethyl acetoacetate or dimethyl malonate(0.5mM) and L-amino acid (0.1mM, 20mol%) in 1ml ofethanol was taken. The resulting reaction mixture was stirredat room temperature for the time mentioned in Tables1, 2, 3, 4, 5. Progress of the reaction was checked using TLC.After completion of the reaction, ethanol was evaporatedand 5ml of water was added. Then the product was extractedwith dichloromethane. The combined organic layers weredried over anhydrous Na2SO4and evaporated to afford crudeproduct, which was purified by simple washing with smallamount of cold ethanol to obtain pure product. The collectedproduct was found to be pure enough and subjected to standardanalytical techniques such as NMR, IR and elementalanalysis.
With piperidine at 20℃;
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  • [ 538-51-2 ]
  • [ 883-93-2 ]
YieldReaction ConditionsOperation in experiment
75% With tert.-butylhydroperoxide; sulfur; potassium iodide In water; dimethyl sulfoxide at 130℃; for 24h;
6% With ammonium iodide; sulfur In sulfolane at 200℃; for 24h; Inert atmosphere; 7. Reaction of N-Benzylideneaniline (6) with Sulfur (Scheme 6c) Using a 15 mL oven-dried reaction vessel, the reaction of N-Benzylideneaniline (6) (362mg, 2.0 mmol), powdered sulfur (321 mg, 10.0 mmol), NH4I (435 mg, 3.0 mmol), andsulfolane (2.0 mL) was performed at 200 °C (oil bath) for 24 h under an argonatmosphere. The yield of 3aa was obtained in 6% GC yield based on 6.
With sulfur
With sulfur Heating;

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YieldReaction ConditionsOperation in experiment
100% With polymer-bound NADH (2a)
100% With Hantzsch ester In ethanol for 24h;
100% With Hantzsch ester; mesoporous silica In benzene at 25℃; for 1h;
100% With poly(p-aminostyrene)-palladium(II); hydrogen In N,N-dimethyl-formamide at 25℃;
100% With potassium-t-butoxide; hydrogen; potassium isopropoxide at 20℃; for 4h;
100% With potassium-t-butoxide; hydrogen; potassium isopropoxide at 20℃; for 4h;
100% With hydrogen In ethanol at 100℃; Flow reactor; Green chemistry; chemoselective reaction;
100% With hydrogen In lithium hydroxide monohydrate; ethyl acetate at 40℃; for 3h;
100% With C24H29ClN5Ru(1+)*BF4(1-); potassium-t-butoxide In isopropanol for 4h; High pressure; Inert atmosphere; Molecular sieve; Reflux;
100% With dichloro[N,N-(2,6-pyridinediyl-kN)dimethylidyne]bis[2-methyl-2-propanamine-kN](triphenylphosphine)ruthenium; sodium tertiary butoxide at 140℃; for 20h;
100% With trans-RuCl2(PPh3)[PyCH2NH(CH2)2PPh2]; potassium-t-butoxide; hydrogen In tetrahydrofuran at 40℃; for 16h;
99% In toluene at 25℃; for 24h; 4.4. General procedure for the reduction of aldehydes and imines General procedure: To a stirred solution of aldehyde or imine (6, 1 mmol) in toluene (2 mL) were added PdO-Fe3O4 (50 mg, 1.2 mol % of Pd) and PMHS (2 mmol, 0.12 mL). The resulting mixture was stirred at room temperature during two days. The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The corresponding products 3a or 7 were purified by chromatography on silica gel (hexane/ethyl acetate).
99% With benzylic alcohol In o-dimethylbenzene at 144℃; for 1h; Inert atmosphere;
99% With Au0998Ag0002; hydrogen In ethanol at 90℃; for 24h; chemoselective reaction;
99% With Hantzsch ester; cyclopenta[2,1-b;3,4-b’]dithiazole-4-one In dichloromethane-d2 at 20℃; Inert atmosphere;
99% With sodium tetrahydridoborate; Orthoboric acid In tetrahydrofuran; methanol at 0 - 20℃; General procedure for the synthesis of amines (4a-4g) NaBH4 (1.1 equiv.) then, H3BO3 (1.0 equiv.) were slowlyadded to a solution of imine 3a-g (1.0 equiv.) in MeOH: THF (1:1) stirred at 0 °C and monitored by TLC. Thereaction mixture was washed three times with NaHCO3:CH2Cl2, the organic phases dried over anhydrous Na2SO4,and evaporated under reduced pressure. The product wasrecrystallized from CH2Cl2/petroleum ether.N-benzylaniline (4a) Yield: 99%; white crystals; mp 49-50 °C; 1H NMR (300 MHz, CDCl3): δ 7.47-7.24 (m,5H, H-9, H-10, H-11, H-12, H-13), 6.78-6.45 (m, 5H, H-3,H-4, H-5, H-6, H-7), 4.25 (s, 2H, H-1), 3.98 (s, 1H, NH);13C NMR (75 MHz, CDCl3): δ 148.5 (C-8), 139.8 (C-2),129.6 (C-4, C-6), 128.9 (C-3, C-7), 127.8 (C-10, C-12),127.5 (C-5), 117.8 (C-11), 113.2 (C-9, C-13), 48.6 (C-1).
99% With C21H25BrN2Ru; isopropanol; potassium hydroxide for 24h; Reflux; Molecular sieve;
99% With lithium diisobutyl-tert-butoxyaluminum hydride; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 50℃; for 24h; Inert atmosphere;
99% With 1-Methylpyrrolidine; C13H12MnN3O5; hydrogen In tetrahydrofuran at 100℃; for 24h; Autoclave; Glovebox;
99% With sodium hydride; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;
99% With benzylic alcohol
99% With hydrogen In methanol at 25℃; for 8h;
98% With zinc(II) tetrahydroborate In diethyl ether for 1h; Ambient temperature; other Schiff bases; application to Tandem Alkylation-Reduction to Nitriles;
98% With pentacarbonyliron(0); carbon monoxide; hydrogen In methanol at 150℃; for 3h; other solvents, var. pressure of CO, var. Fe(CO)5 concentration, var. temperature;
98% With zinc(II) tetrahydroborate In diethyl ether for 1h; Ambient temperature;
98% With potassium hydroxide; isopropanol for 10h; Heating;
98% With isopropanol In benzene at 70℃; for 5h;
98% With borane-ammonia complex In tetrahydrofuran at 65℃; for 4h;
98% With [Ir(I)(cod)(NHC-Trzl)+]OTf-; potassium-t-butoxide; isopropanol at 80℃; for 23h; Schlenk technique; Inert atmosphere;
98% With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8H(1-); hydrogen In toluene at 80 - 90℃; for 5h;
98% With triethylsilane; C34H33ClIrP; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 40℃; for 2h; Schlenk technique; Inert atmosphere;
98% With sodium tetrahydridoborate In methanol Sodium borohydride (300.0 mg, 7.92 mmol, 2.0 equiv.) was added to a solution of benzylideneaniline (715.0mg, 3.95 mmol, 1.0 equiv.) in methanol (20 mL) and the mixture was stirred over night until TLC confirmed fullconversion of the starting material. The solvent was removed under reduced pressure and the crude productwas purified by column chromatography (LP/EA 4:1, 40 g silica). The desired product (10) was obtained as acloudy oil (710.5 mg, 3.88 mmol, 98%).
98% With 6C53H32O8(4-)*13Zr(4+)*18O(2-)*8Co(2+)*8Cl(1-); hydrogen; sodium triethylborohydride In toluene at 80℃; for 5h; 15 Example 15
Catalytic Hydrogenation of Imines and Carbonyls with Zr-MTBC-CoH
General procedure: Prompted by the hydrogenation of the carbonyl group of methylheptenone at elevated temperatures, the hydrogenation of imines and carbonyls with Zr-MTBC-CoH was studied. See Scheme 21. Zr-MTBC-CoH displayed excellent activity in catalytic hydrogenation of imines. See Table 18, below. Though hydrogenation of imines is an important synthetic route to amines, examples of base metal catalysts for imine hydrogenation are rare. See Zhanq et al., Organometallics, 2015, 34, 2917-2923. The present imine hydrogenation reactions were performed in toluene at 80° C. under 40 bar of H2 in presence of 0.5 mol % Zr-MTBC-CoH. N-benzylideneaniline was completely hydrogenated to N-benzylaniline in 5 h. The pure product was isolated in 98% yield after simple filtration followed by removal of the volatiles in vacuo. See entry 1, Table 18. The Zr-MTBC-CoH recovered after this reaction remained crystalline, as shown by PXRD. See FIG. 16B, and the leaching of Co and Zr into the supernatant was 0.23% and 0.08%, respectively. N-(4-chlorobenzylidene)benzenamine, N-(2-methoxybenzyli-dene)benzenamine, N-(4-methoxybenzylidene)benzenamine and N-benzylidenebenzylamine were efficiently reduced within 24 h to afford corresponding N-benzylanilines in excellent yields. See entries 2-5, Table 18. The hydrogenation of trisubstituted imines, such as (E)-N-(1-phenylethylidene)aniline, however, required longer reaction times (see entry 7, Table 18), presumably due to the decreased rates of diffusion of the larger substrate and product through the MOF channels and less facile binding and activation of the substrate.
98% With (4-Ph)Triaz(NHP<SUP>i</SUP>Pr<SUB>2</SUB>)<SUB>2</SUB>Mn(CO)<SUB>2</SUB>Br; potassium-t-butoxide; hydrogen In tetrahydrofuran at 50℃; for 4h; Glovebox; Autoclave; Sealed tube; chemoselective reaction;
98% With potassium-t-butoxide; C38H37ClN2PRu(1+)*C32H12BF24(1-); benzylic alcohol In neat (no solvent) at 70℃; Sealed tube; Inert atmosphere; Schlenk technique; Green chemistry;
97% With Bu2SnClH-HMPA In tetrahydrofuran for 1h; Ambient temperature;
97% With chloro(η5-pentamethylcyclopentadienyl)(L-prolinato)iridium(III); isopropanol In toluene at 85℃; for 4h;
97% With trimethylamine-N-oxide; (N,N,N-trimethyl-2-(5-oxo-4,6-bis(trimethylsilyl)cyclopenta[c]pyrrol-2-(1H,3H,5H)-yl)ethanaminium) iron tricarbonyl; hydrogen In lithium hydroxide monohydrate at 85℃; for 14h; Autoclave; Inert atmosphere;
97.4% With sodium tetrahydridoborate In methanol at 10℃; N-Benzylaniline (compound 4) Compound 3 (2.00 g, 11.0 mmol, 1 eq) was dissolvedin 30ml methanol. The solution was cooled to -10 C, then sodium borohydride (1.66g, 44 mmol, 4 eq) was gradually added in by small portion. The reaction was kept at 10C overnight, then evaporated and extracted with dichloromethane followed by washingwith 20ml DI water for 3 times. The organic phase was separated from the aqueouslayer and the solvent was evaporated to yield pure compound 4 (1.96 g, 10.7 mmol,yield: 97.4%). 1H NMR (400 MHz CDCl3, δ): 7.43-7.37 (m, 4H), 7.33-7.29 (m, 1H),7.24-7.20 (m, 2H), 6.79-6.75 (m, 1H), 6.70-6.68 (d, 2H), 4.37 (s, 2H).
97% With C20H26ClIrN3O(1+)*F6P(1-); benzylic alcohol In lithium hydroxide monohydrate at 110℃; Inert atmosphere; Schlenk technique; Glovebox;
97% With 4,4,5,5-tetramethyl-1,3,2-dioxaborolane; lithium bromide In tetrahydrofuran at 20℃; for 1h; chemoselective reaction;
97% With C29H43FeN5O3 In isopropanol at 80℃; for 16h;
96% With BH3 In methanol for 0.5h; Ambient temperature;
96% With LiCrH4*2LiCl*2THF In tetrahydrofuran at 25℃; for 12h;
96% With dodecacarbonyltri-iron In toluene at 100℃; for 24h; Inert atmosphere;
96% With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; for 24h; chemoselective reaction;
96% With C40H41BF10PSi(1-)*H(1+); hydrogen In dichloromethane-d2 at 50℃; for 24h; Autoclave;
96% With phenylsilane; C43H44FeN2O4 In dimethyl sulfoxide at 25℃; for 12h; Schlenk technique;
96% With C13H8BrMnN2O5; potassium-t-butoxide In isopropanol at 80℃; for 24h; Inert atmosphere; Sealed tube;
96% With hydrogen In toluene at 140℃; for 48h; chemoselective reaction;
96% With hydrogen In ethanol at 30℃; 1-3 Example 1: Synthesis of N-benzylaniline In a solvent of ethanol (2 mL) with PdNPore (2.7 mg, 5 mol%) catalyst, Add the substrate N-benzenylphenylimine (90.5 mg, 0.5 mmol), Connect a balloon filled with hydrogen and place it on a magnetic stirrer for 30 hours at 30 ° C. Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate = 10: 1, 3% triethylamine was added to the developing agent) to obtain 87.9 mg of N-benzylaniline, The yield was 96%.
95% With hydrogen In tetrahydrofuran at 100℃; for 18h;
95% With tetrakis[3,5-bis(trifluoromethyl)phenyl]boric acid bis(diethyl ether) complex; (PNP<SUP>Cy</SUP>)Co(CH<SUB>2</SUB>SiMe<SUB>3</SUB>); isopropanol In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;
95% With methanol; C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Sealed tube; Inert atmosphere;
95% With Hantzsch ester In chloroform-d1 at 20℃; for 0.166667h;
95% With C17H27Cl2NRuS2; HSiPh3 In ethanol at 20℃; for 0.25h; chemoselective reaction;
95% With boron trifluoride diethyl ether complex; 2,6-dimesityl-1-methyl-4-phenyl-1,4-dihydropyridine In diethyl ether at 30℃; for 2h; Inert atmosphere; Schlenk technique;
94% With hydrogenchloride; Zr(BH4)2Cl2(dabco)2 In methanol for 0.5h; Heating;
94% With hydrogen for 0.666667h;
94% With 1-butyl-3-methylimidazolium tetrachloroferrate(III); diphenylsilane In ethanol at 80℃; for 16h;
93% With benzenetellurol In tetrahydrofuran Heating; -78 deg C -> RT, 0.5 h; other reagents, solvent;
93% With 2-(4'-carboxyphenyl)benzothiazoline; trifluoroacetic acid In acetonitrile at 20℃; for 22h; Inert atmosphere; 3. General procedure for the transfer hydrogenation General procedure: (a) Procedure for the reduction of imines. TFA (0..4 mmol) was added to a mixture of imine (0.2 mmol) and benzothiazoline(0.24 mmol) in CH3CN (2 mL) under nitrogen. The reaction mixture was stirred at room temperature until the imine was consumed, which was monitoring by TLC.The reaction was stopped by addition of water and the reaction mixture was extracted by EtOAc and the mixed organic extracts were washed with 10% NaOH solution for three times to remove the residual benzothiazoline and generated benzothiazole. Concentration of the the solvent gave the crude product of amine. If necessary, theproduct could be further purified by flash column chromatography.
93% With Lithium amidotrihydroborate In tetrahydrofuran at 20℃; for 2h; closed bottle; 2 5 ml solution of 0.1 M LiNH2BH3 in THF was slowly added into lml solution of 0.5 M N-benzylideneaniline in THF under room temperature in a closed glass bottle. FTIR spectrometer was used to observe the consumption of imine group and formation of amine group. The reaction was stopped two hours later. Analysis indicated conversion of N-benzylideneaniline is over more than 99%. THF was evaporated by rotary, then 10 ml hexane was added into the glass bottle to extract amine formed residues for two times. Then, clear hexane solution was collected after centrifugation. Next, hexane was removed with the rotary evaporation evaporated to leave rude product. In the end, further column chromotrography was utilized to purify rude amine product to obtain the end product. The isolated yield of N-benzylaniline is more than 93%. In-situ FTIR (in FIG. 2) show that during the reaction, absorption of C=N stretch vibration at 1631 cm-1 was decreasing accompanied with increasing absorption of NH stretch vibration at 3369 cm-1. (see FIG. 2) Characteristic data of product: 1H NMR (500 MHz, CDCl3): δ(ppm) 4.05 (s, N-H), 4.36 (s, 2H), 6.67-6.78 (m, 3H), 7.20-7.42 (m, 7H); 13C NMR (500 MHz, CDC13): δ (ppm) 48.31, 112.84, 117.55, 127.19, 127.48, 128.60, 129.23, 139.45, 148.15;FT-IR (neat): 3419, 2920, 1602, 1505, 750 cm-1.
93% With ruthenium(III) trichloride trihydrate; potassium carbonate; propane-1,2,3-triol at 130℃; for 24h; Inert atmosphere; Sealed tube; 4.3. The procedure of two-step route. Step 2. General procedure: A mixture of imine (0.5mmol), RuCl3·3H2O (3.0mol%), K2CO3 (0.5mmol) and glycerol (5.0mmol) was stirred at 130°C for 24h in a sealed tube under a nitrogen atmosphere. Workup and purification was as the same as Step 1.
93% With (Ru(1,2:5,6-η-1,5-cyclooctadiene)(η(3)-methallyl)2); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 130℃; for 24h;
93% With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In isopropanol; acetonitrile at 100℃; for 24h; Autoclave; Glovebox; chemoselective reaction;
92% With hydrogen In ethanol at 20℃; for 4h; 3. Applications of treated catalysts in hydrogenation reactions. General procedure. General procedure: A mixture of substrate (0.2 mmol) and Pd/Al2O3Si (6.4 mg, 1 mol%) in ethanol (2 mL) was stirred under hydrogen atmosphere (H2 balloon pressure) at room temperature. The progress of reaction was monitored by TLC analysis or GC-MS. After the reaction was completed, the reaction mixture was filtered, and the catalyst was washed with ethanol. The solvent in filtrate was removed by vacuum to give the crude product. The purified product was obtained by column chromatography or recrystallization. After each cycle, the palladium residue in the reaction mixture solvent was determined by ICP-OES.
92% With C13H23BN2 In toluene at 25℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox;
92% With phenylsilane; C12H37CoP4(1+) In toluene at 110℃; for 1h;
91% With C56H55ClN3P2Ru(1+)*F6P(1-); potassium 2-methyl-2-butoxide In isopropanol at 20 - 80℃; for 1.5h; Schlenk technique; Inert atmosphere;
91% With cobalt nanoparticles In tetrahydrofuran Heating; High pressure;
91% With C24H30Cl2NPRuS2; potassium-t-butoxide; hydrogen In dichloromethane; toluene at 80℃; for 5h; Autoclave;
91% With [Mn(CO)3Br(κ2N,N-PyCH2NH2)]; potassium-t-butoxide; isopropanol at 80℃; for 3h; Schlenk technique; Inert atmosphere;
91% With hydrogen In N,N-dimethyl acetamide at 20℃; for 18h;
90% With Hantzsch ester; trifluoroacetic acid In dichloromethane In the dark.;
90% Stage #1: benzylidene phenylamine With samarium; samarium(III) trichloride In N,N-dimethyl acetamide; lithium hydroxide monohydrate at 20℃; for 8h; Stage #2: With hydrogenchloride In N,N-dimethyl acetamide; lithium hydroxide monohydrate
90% With Hantzsch ester In toluene at 70℃; for 24h; Inert atmosphere;
90% With Dimethylphenylsilane; gold nanoparticles; lithium hydroxide monohydrate In acetonitrile at 20℃; for 5h; chemoselective reaction;
90% With Hantzsch ester; C40H38I2N4(2+)*2CF3O3S(1-) In dichloromethane at 20℃; for 1h; Inert atmosphere;
90% With triethylsilane; Ir(Cp*)(phpy)Cl; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 25℃; for 0.25h; Inert atmosphere;
90% With C23H25IIrN3; hydrogen In 2,2,2-trifluoroethanol at 35℃; for 6h;
90% With hydrogen; lithium hexamethyldisilazane In toluene at 80℃; for 21h; Inert atmosphere; Autoclave;
90% With manganese(I) pentacarbonyl bromide; hydrogen In tetrahydrofuran at 130℃; for 8h;
88% With polymeric xylylene-ionene borohydride In methanol at 20℃; for 3.5h;
88% With sodium tetrahydridoborate In ethanol at 20℃; for 8h; Synthesis of secondary amines catalysed by the CeCl3·7H2O-NaBH4system; general procedure Benzaldehyde (1.0 mmol), amine (1.2 mmol) and CeCl3·7H2O (0.02mmol) in ethanol (5 mL) were stirred for 20 min at room temperature,then NaBH4 (2 mmol) was added. On completion of the reaction (asmonitored by TLC), the reaction mixture was dried under vacuumand the product was extracted with ethyl acetate (3 × 10 mL).Evaporation of the solvent gave a crude product which was purifiedon a small silica gel column with EtOAc: petroleum ether (10:1) as eluent
88% With 4-fluorobenzenethiol In toluene for 8h; Sealed tube; Irradiation;
88% With Triethoxysilane; [bis(2,6-diisopropylaniline)acenaphthene]Fe(η6-toluene) at 70℃; for 4h; Schlenk technique; Inert atmosphere; Glovebox; Sealed tube;
88% With cis-tetracarbonyl(1,1'-methylene-3,3'-dimethyl-4,4'-diimidazoline-2,2'-diylidene)molybdenum(0); potassium-t-butoxide; benzylic alcohol In hexane at 130℃; for 24h;
88% With 1,1,3,3-Tetraphenyl-1,3-di-λ5-phospha-1,2-cyclohexadien; 4,4,5,5-tetramethyl-1,3,2-dioxaborolane In benzene for 1h; Glovebox; Inert atmosphere;
87% With hydrogen; diisobutylaluminium hydride In toluene at 100℃; for 24h;
87% With dimethylsulfide borane complex In chloroform-d1 at 60℃; for 2h; Sealed tube; Schlenk technique; chemoselective reaction; General procedure for reduction of imines General procedure: After 1.0 mmol of an imine (entries 1-12) and Me2S-BH3 (amounts according to Table 1) were mixed in a sealed J. Young NMR tube using about 1 mL of CDCl3, the reaction mixture was left at 60 °C for the time duration indicated in Table 1. For α,β-unsaturated imines (entries 13 and 14), the reactants were mixed in CH2Cl2 at -78 °C. After the reaction was completed (via 1H-NMR spectroscopy), it was quenched with 5 mL of MeOH, followed by removal of all volatiles under reduced pressure. The crude product mixture was then dissolved in 10 mL ethyl acetate, washed three times with 10 mL of water/brine, and dried with MgSO4. All amine samples were collected as oils after removal of solvent apart from benzylmethylamine (entry 1) and N-benzylaniline (entry 4), which were obtained as solids. The spectroscopic data for all amines matched those reported (Table 2).
86% With anhydrous magnesium perchlorate; Hantzsch ester In tetrahydrofuran for 16h; Heating;
86% With [RuCl(PPh3)2(3-phenylindenyl)]; 1,1,1,3,3,3-hexamethyldisilazane potassium; isopropanol at 89℃; for 1h; Glovebox;
86% With triethylsilane; palladium diacetate In ethanol for 0.5h; Inert atmosphere;
86% With hydrogen In methanol at 20℃; for 7h; chemoselective reaction;
85% With anhydrous sodium carbonate; isopropanol for 0.5h; Heating;
85% With triethylsilane; zinc In methanol at 20℃; for 0.333333h; Inert atmosphere; chemoselective reaction;
85% With borane-THF In tetrahydrofuran at 20℃; for 1h;
85% Stage #1: benzylidene phenylamine With [RuVI(N)(N,N’-bis(salicylidene)-o-cyclohexyldiamine dianion)(CH3OH)][ClO4]; phenylsilane In toluene for 46h; Reflux; Stage #2: With hydrogenchloride In diethyl ether; lithium hydroxide monohydrate; toluene
85% With tri-n-octylmethylammonium chloride; sodium hydroxide; zinc In lithium hydroxide monohydrate at 20℃; for 0.67h;

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  • 12
  • [ 100-52-7 ]
  • [ 62-53-3 ]
  • [ 538-51-2 ]
YieldReaction ConditionsOperation in experiment
100% In chloroform Ambient temperature;
100% In toluene at 120℃; for 24h;
100% With alumina-entrapped Ag at 120℃; for 1h; Inert atmosphere; Autoclave;
100% at 20℃;
100% With triethylamine In 1,2-dichloro-ethane at 60℃; for 0.5h;
100% With aluminum(III) oxide for 5h; Milling; Aldimines 2a-g, 4; General Procedure General procedure: The required amine (10 mmol) was stirred with slow-basic chromatographic Al2O3 (3 g). Aldehyde (10 mmol for 2a-g or 20 mmol for 4) was stirred with slow-basic chromatographic Al2O3 (3 g). The aldehyde dispersed on alumina was added by portions to the amine dispersed on alumina upon grinding and then the mixture was allowed to stay for 5 h. The aldimine formed was extracted with CH2Cl2 (2 × 25 mL) and the combined extracts were evaporated under reduced pressure to give the desired product in almost quantitative yield.
100% In ethanol for 1h; Sonication; General Procedure for the Synthesis of the Starting Imines 6 General procedure: To a solution of benzylamine (1.0 equiv) in EtOH (7.8 mL per mmol) was added the corresponding aldehyde (1.0 equiv). The reaction was sonicated for 60 min before being concentrated in vacuo. Water was added and the organics were extracted with DCM, combined, dried over MgSO4, filtered and concentrated in vacuo to afford the desired pure imine.
100% With N-doped graphene-based manganese nanocatalyst In n-octane at 140℃; for 2h;
99% With aluminum(III) oxide at 20℃; for 2h;
99% With toluene-4-sulfonic acid
99% With 4 A molecular sieve; Sodium hydrogenocarbonate In benzene Heating;
99% With trimethylsilanecarbonitrile; [In(O2C2H4)0.5(4,4′-(hexafluoroisopropylidene)bis(benzoicacid))] In neat (no solvent) at 20℃; Schlenk technique;
99% at 90 - 120℃; Irradiation; General procedure for the synthesis of imines (3a-3g) Imines 3a-3g were prepared using the methodology ofDelgado et al. (Vzquez et al. 2004). Briefly, amine 2 (1equiv.) and aldehyde 1 (1.05 equiv.) were placed in a roundbottom flask. This mixture was irradiated with infrared lightwith a lamp intensity of 30-40 volts (90-120 °C) and thereaction monitored by TLC. The crude reaction mixture was washed with hexanes and crystallized from cold hexanes ora mixture of cold dichloromethane/hexanes. N-Benzylidenaniline (3a) Yield: 99%; pale yellow crystals;mp 51-52 °C; 1H NMR (300 MHz, CDCl3): δ 8.47 (s,1H, H-1), 7.92 (dd, J = 6.5, 2.9 Hz, 2H, H-9, H-13), 7.47(dd, J = 11.5, 7.8 Hz, 5H, H-3, H-4, H-5, H-6, H-7), 7.24 (t,J = 7.1 Hz, 3H, H-10, H-11, H-12).
99% With HC(CMeN(2,6-Et2C6H3)2)Al(μ-S)2AlHC(CMeN(2,6-Et2C6H3))2 In chloroform-d1 at 20℃; Inert atmosphere; (2) General procedures for the catalytic reactions of aldimine condensation reaction General procedure: The selected amine (1 mmol) and the chosen aldehyde (1 mmol) were added in CDCl3 (3 ml) consecutively while the catalyst 1 (0.05 mmol) was placed before in the reaction flask. The resulting mixture was reacted at room temperature within 2 h. The reaction mixture was filtered and the solvent removed under vacuum to yield the desired product.
99% In ethanol at 20 - 80℃; for 68h; Schlenk technique; Inert atmosphere; A V.1 N-Phenylbenzyl-amine (10) Benzaldehyde and aniline were distilled at reduced pressure prior to use. Aniline (370.0 mg, 3.97 mmol, 1.0equiv.) and benzaldehyde (428.0 mg, 4.02 mmol, 1.02 equiv.) were dissolved in 20 mL ethanol in a flame driedSchlenk flask under argon atmosphere. The reaction was heated for 4 h to 80 °C (oil bath) and was stirred 64 hat r.t.. The solvents were removed under reduced pressure to give the product as colorless oil (715.0 mg, 3.95mmol, 99%), which was used without further purification. [Rf: 0.14 (LP/EA 10/1), 1H NMR (400 MHz, CDCl3) δ =8.43 (s, 1H, C=N), 7.90 - 7.86 (m, 2H, CH2), 7.58 - 7.08 (m, 10H, Ar-H) ppm].
98% With Montmorillonite K 10 clay for 0.05h; microwave (800 Watts) irradiation at ca. 110 deg C;
98% at 50 - 52℃; for 0.0111111h; microwave irradiation;
98% at 60℃; for 2h;
97% for 0.25h;
97% for 0.0166667h; Irradiation;
97% In lithium hydroxide monohydrate at 20℃; for 2h;
97% In dichloromethane at 20℃; Molecular sieve;
97% With carbon dioxide at 25℃; for 24h; Autoclave;
96% With 1-n-butyl-3-methylimidazolium tetrafluoroborate at 20 - 50℃; for 3h;
96% With gold nanoparticles supported on titanium dioxide (TiO<SUB>2</SUB>); isopropanol In toluene at 120℃; for 14h; Inert atmosphere;
96% In methanol
96% With hydrotalcite; oxygen In lithium hydroxide monohydrate at 40℃; for 24h; Schlenk technique;
96% In neat (no solvent) at 25℃; General procedure for the preparation of N-benzylideneamines General procedure: A mixture of 25 mmol of amine [butylamine (2.5 mL), cyclohexylamine (2.9 mL), aniline(2.3 mL)] and 25 mmol of aldehyde [benzaldehyde (2.6 mL), 2-chlorobenzaldehyde (2.8 mL),3-chlorobenzaldehyde (2.8 mL), 4-chlorobenzaldehyde (3.5 g)] was stirred for 6-10 min at rt(25 °C). After completion, 10 mL of dichloromethane were added to the mixture, dried(Na2SO4) and filtered. Evaporation of the volatile components provided the products 1a-f.
96% With glacial acetic acid In toluene at 110℃; for 16h; Dean-Stark; Inert atmosphere;
95% With 4 A molecular sieve In dichloromethane for 1h; Ambient temperature;
95% With magnesium(II) sulfate In benzene for 0.5h; Ambient temperature;
95%
95% With aqueous extract of pericarp of Sapindus trifoliatus fruits at 20℃; for 0.0833333h;
95% With montmorillonite at 20℃; for 0.166667h; Neat (no solvent);
95% With urea-choline chloride deep eutectic mixture at 60℃; for 2h; Green chemistry; General procedure for the synthesis of imines in DES(Table 2) General procedure: In a dried test tube, 1.0 mmol aldehyde, 1.0 mmol amine,and 0.2 cm3 DES were added and the mixture was heatedat 60 C until the reaction was completed. After the reactiontime, water was added to the mixture, and the residuecollected by filtration. The resulting solid was washed withwater and was purified by flash column chromatography orrecrystallization with ethanol to give pure products. Theviscous oil/semi-solid products were extracted with ethylacetate. All compounds were characterized by meltingpoints that were found to be identical with the ones describedin literature.
95% In lithium hydroxide monohydrate at 25℃; for 3h; Inert atmosphere;
95% In methanol at 20℃; Flow reactor; Automated synthesizer;
94% With glacial acetic acid In methanol Reflux;
93% Ambient temperature;
93% With TiO2 supported on Au In ethanol at 139.84℃;
93% In dichloromethane at 20℃; for 16h; Molecular sieve;
93% In methanol at 60℃; for 0.5h; Microwave irradiation; Imines and Iminoesters 5; General Procedure General procedure: In a 25 mL round-bottomed flask were mixed the corresponding aniline (4.0 mmol), aldehyde (4.4 mmol, 1.1 equiv), and MeOH (ca. 3.0mL). The reaction mixture was irradiated by microwave energy in an open vessel (150 W) at 60 °C for 30 min. The reaction progress wasmonitored by TLC. Upon completion, the mixture was cooled to r.t. and MeOH was removed under reduced pressure. The pure product was precipitated with a DCM/hexane mixture (5:95). N-Benzylidenaniline (5a)Yellow solid; yield: 1.088 g (93%); mp 51-52 °C.1H NMR (500 MHz, CDCl3): = 8.28 (1 H, s, HC=N), 7.82-7.80 (2 H, m,H-8, H-12), 7.33-7.29 (5 H, m, H-2, H-6, H-9, H-10, H-11), 7.27-7.13(3 H, m, H-3, H-4, H-5).13C NMR (125 MHz, CDCl3): = 160.5 (C=N), 152.2 (C-1), 136.4 (C-7),131.6 (C-10), 129.4 (C-8, C-12), 129.1 (C-3, C-5), 129.0 (C-9, C-11),126.2 (C-4), 121.2 (C-2, C-6).Spectral data are consistent with the literature.51
92.4% at 50℃;
92% In lithium hydroxide monohydrate at 60℃; for 5h;
92% at 20℃; for 4h;
90% In methanol for 16h;
90% With anhydrous magnesium perchlorate at 20℃; for 0.166667h; N-Benzylideneaniline (II) This compound was synthesized by following the reported procedure. A mixture of 1a (0.42 g, 4 mmol), and 2a (0.36 g, 4 mmol) wasstirred magnetically at r.t. in the presence of Mg(ClO4)2 (40 mg, 0.2mmol, 5 mol%). After completion of the reaction (10 min, TLC), thecrude mixture was crystallized (EtOH) to afford the product (0.655 g,90%) as a yellow solid; mp 120-123 °C.
90% With 4-hydroxy-1-methyl-2(1H)-quinolone; glacial acetic acid at 20℃; for 2h;
90% With C34H44Al2N4S3 In chloroform-d1 at 20℃; 3.5.2. General procedure for the catalytic reactions of aldehydes with amines. General procedure: The selected aldehyde (1 mmol) and the chosen amine (1 mmol) were added in CDCl3 (3 ml) consecutively while the catalyst 1(0.03 mmol) was placed before in the reaction flask. The resulting mixture was reacted at room temperature within 2 h (Scheme 3). The reaction mixture was filtered and the solvent removed under vacuum toyield the desired product. Quantitative formation of the products given in Scheme 3 were confirmed, and the spectroscopic data for the products were identical to the reported literature data [72].
89% With trifluoroacetic acid In ethanol at 90℃; for 12h;
89% With trifluoroacetic acid In ethanol at 90℃; for 12h;
89% With magnesium(II) sulfate In dichloromethane for 16h; Sealed tube; Inert atmosphere;
88% With sodium hydroxide In toluene at 110℃;
86%
86% In ethanol for 3h; Reflux;
86% With hydroxylamine hydrochloride supported on melamin formaldehyde for 0.0833333h; Microwave irradiation; neat (no solvent);
86% With trichloroacetic acid In ethanol at 25℃; for 1h;
86% With glacial acetic acid In ethanol for 68h; Inert atmosphere; Reflux;
85.9% In ethanol at 78℃; for 5h; Synthesis of imine Schiff-base ligands General procedure: An appropriate quantity of 4-Hydroxy benzaldehyde (or 3-nitrobenzaldehyde, or 4-nitrobenzaldehyde, or salicylaldehyde, or benzaldehyde) (0.02 mol) was added into a 100-ml round-bottom flask filled with 30 ml of absolute ethanol under stirring. The resulting mixture was refluxed at 78 °C until the dissolution of 4-hydroxy benzaldehyde. Subsequently, 0.02 mol of benzylamine (or aniline) was slowly dripped into the above solution while stirring. Then, the refluxing was kept for another 5 h until the completion of reaction. After the solution was cooled down to -5 °C, a coarse product was recovered by filtration, which, then, underwent further re-crystallization with ethanol to obtain purely crystalline 4-hydroxyl benzaldehyde benzylimine (L8), (or 4-nitro benzaldehyde benzylimine (L9), or 3-nitro benzaldehyde benzylimine (L10), or salicylaldehyde phenylimine (L11), or benzaldehyde phenylimine (L12))
85% In toluene Dean-Stark; Reflux; Inert atmosphere;
84% for 0.5h;
84% In dichloromethane for 18h; Molecular sieve;
83% In ethanol at 20℃; for 3h; Inert atmosphere;
81% With Sodium sulfate [anhydrous] In dichloromethane N,2-diphenylethane-1-imine (36) Aniline (0.0462 mol, 5.00 g) was added dropwise (about 5 minutes) to a mixture of benzaldehyde (0.0462 mol, 4.32 g) and Na2SO4 (0.0282 mol, 4.00 g) under vigorous stirring in a 250 mL round-bottomed flask (exothermy was detected). After 10-15 minutes, the mixture solidified and was left under stirring for further 10 min. The solid was then dissolved in the minimum amount of dichloromethane and the inorganics filtered off. The filtrate was evaporated under vacuum to give an orangish solid, which was treated with cold petroleum ether (20 mL). The precipitate was grinded and filtered under vacuum, washed with cold petroleum ether (2 x 5 mL) to give the pure imine compound 31 (6.78 g, 81%). 1H NMR (600 MHz, CDCl3, 25 °C): δ = 7.23-7.31 (m, 3H), 7.40-7.46 (m, 2H), 7.47-7.54 (m, 3H), 7.92-7.98 (m, 2H), 8.48 (s, 1H). 13C{1H} NMR (150 MHz, CDCl3, 25 °C): δ = 121.0, 126.1, 128.9, 128.9, 129.3, 131.5, 136.3, 155.2, 160.6. EI-MS m/z (%): 181 (M+, 85), 180 (100), 77 (35), 51 (12).11
80% at 20℃; for 0.5h;
80% With Aluminum Chloride; dihydrogen peroxide In dichloromethane; lithium hydroxide monohydrate at 25℃; Inert atmosphere;
80% In ethanol
79.67% With oxygen In acetonitrile at 30℃; for 12h; Inert atmosphere; Sealed tube;
77% In ethanol Heating;
76% With magnesium(II) sulfate In tetrahydrofuran at 25℃; for 24h; N-Benzylideneaniline (compound 3) N-Benzylideneaniline (compound 3): Benzaldehyde (2.00 g, 18.8 mmol, 1 eq), aniline(1.76 g, 18.9 mmol, 1 eq), anhydrous magnesium sulfate (5 g) and tetrahydrofuran(50ml) were added to a round bottom flask. The reaction mixture was stirred at 25 Cfor 24 h before filtration. The filtrate was concentrated via rotary evaporation, and theresulting solid was recrystallized in DCM/hexane to yield compound 3 as pale yellowsolid (2.6 g, 14.3 mmol, yield: 76 %). 1H-NMR (400 MHz CDCl3, δ): 8.14 (s, 1H),7.60-7.59 (m, 2H), 7.17-7.15 (m, 3H), 7.10-7.07 (m, 2H), 6.94-6.90 (m, 3H).
76% With magnesium(II) sulfate In dichloromethane for 20h; Reflux;
75% for 0.5h;
75% In benzene Heating;
75% With phosphotungstic acid cesium salt; cyclohexanone In lithium hydroxide monohydrate at 80℃; for 0.666667h;
75% With calcium sulfate hemihydrate In toluene for 5h; Reflux;
74% In diethyl ether for 4.5h;
74% In ethanol for 6h; Reflux;
73% With potassium hydroxide In toluene at 135℃; for 48h;
67% With erbium trifluoromethanesulfonate In dichloromethane at 20℃; for 0.75h;
65% In toluene for 36h; Reflux;
60% In toluene for 16h; Reflux; 4.2.2. N-(4-(Trifluoromethyl)benzylidene)aniline (3b) General procedure: p-(Trifluoromethyl)benzaldehyde (1.36 mL, 10 mmol) and aniline (0.8 mL, 9 mmol) were dissolved in toluene (100 mL) and stirred under reflux for 16 h. The solution was cooled to rt and toluene was removed under reduced pressure. After recrystallization from hexanes the product was obtained as a white solid (1.93 g, 7.75 mmol, 77%).
50% In ethanol at 20℃; for 24h; Synthesis of N-benzylideneaniline (2a) In a round bottom flask, aniline (2.33g, 2.3mL, 2 mmol) and benzaldehyde (2.65g, 2.5mL, 2mmol) were mixed in ethanol (30 mL). This mixture was allowed to react for 24 h under constant stirring and room temperature. The reaction was concentrated by reducing the volume to a half, under reduced pressure. Then, the reaction was refrigerated (~5 C) overnight, to allow crystallization. Afterwards, the solvent was carefully removed and the crystals were solubilized again in ethanol to recrystallize overnight. The solvent was removed again and the crystals were dried at room temperature(50% yield). 1H NMR(200MHz, CDCl3) δ (ppm) 8.54 (s, 1H); 7.90-7.88 (m, 2H); 7.59-7.49 (m, 3H); 7.46-7.39 (d, 2H); 7.32-7.18 (m, 3H). 13C NMR(101 MHz, CDCl3) δ (ppm) 160.4; 152.1; 136.3; 131.4; 129.2; 128.8; 126.0; 120.9. ESI-Q-TOF m/z calc, for [M+H]+ C13H12N+ 182.0964, found 182.0995. IR: v max 3058 cm-1 (C-H), 1673 cm-1 (C=N).
40% Heating;
28% In lithium hydroxide monohydrate at 24.84℃; for 3h; Darkness;
12% With mesoporous silica In ethanol at 20℃; for 0.25h; Sonication;
With potassium pyrosulfate auf dem Wasserbad;
With ethanol
In benzene Heating; azeotropic destillation;
In benzene Heating;
In benzene Heating; Yield given;
In benzene for 2h; Heating;
1.7 g With calcium(II) chloride at 60℃; for 0.5h;
at 80℃; for 0.5h;
30 % Chromat. With aluminium telluride; triethylamine In tetrahydrofuran Heating;
In ethanol
at 60℃;
With molecular sieve In diethyl ether for 1h;
With piperidine In ethanol
In ethanol for 2h; Heating;

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  • [ 1438-16-0 ]
  • [ 538-51-2 ]
  • [ 4992-29-4 ]
  • 14
  • [ 13887-51-9 ]
  • [ 538-51-2 ]
  • [ 13887-43-9 ]
YieldReaction ConditionsOperation in experiment
With zinc
  • 15
  • [ 7677-24-9 ]
  • [ 538-51-2 ]
  • [ 4553-59-7 ]
YieldReaction ConditionsOperation in experiment
98% With [Cd3(H2O)2(C2H2N3)2(SO4)2] In dichloromethane at 0℃; for 2h; Inert atmosphere;
98% With C2H3O7P2(5-)*3H(1+)*2Ag(1+)*C10H8N2*2H2O In dichloromethane at 20℃; for 4h; Inert atmosphere;
97% Stage #1: benzylidene phenylamine With magnesium iodide etherate In dichloromethane at 20℃; for 0.166667h; Stage #2: trimethylsilyl cyanide In dichloromethane at 20℃; for 3h; Synthesis of α-aminonitriles; typical procedure Freshly prepared MgI2 etherate (0.05 mmol) was added to a stirredsolution of benzylideneaniline 1a (0.5 mmol) in CH2Cl2 (5 mL) atroom temperature. After stirring for 10 min, a solution of TMSCN(0.6 mmol) was added dropwise via a syringe. The resultinghomogeneous reaction mixture was stirred at room temperature for3.0 h and quenched by saturated NaHCO3 aqueous solution. Extractivework-up with ethyl acetate and chromatographic purification of thecrude product on silica gel gave the aminonitriles 2a in 97% yield.2-Phenyl-2-(phenylamino)acetonitrile (2a):20 White solid, m.p. 74-75 °C [lit.20 74-76 °C]; IR (KBr): 3369, 2234, 1604, 1490, 1240, 1120 cm-1;1H NMR: δH 4.27 (d, J = 8.4 Hz, 1H), 5.46 (d, J = 8.5 Hz, 1H), 6.83 (d,J = 7.9 Hz, 2H), 6.97-6.70 (m, 1H), 7.33-7.36 (m, 1H), 7.50-7.51 (m, 3H),7.63-7.65 (m, 2H).
95% With polystyrene-supported 1,5,7-triazabicyclo[4,4,0]dec-5-ene In acetonitrile at 20℃; for 3h; Inert atmosphere; Representative experimental procedures for PS-TBD catalyzed cyanosilylation with TMSCN General procedure: To a solution of PS-TBD (3.4 mg, 0.01mmol) in CH3CN (1 mL) was added carbonyl compounds (1.0 mmol) and TMSCN (1.1 mmol) at room temperature. After the reaction was complete (as determined by TLC), EtOAc (5 ml) was added to the mixture and PS-TBD was separated by filtration. The filtrate was concentrated under vacuum and purified by column chromatography on silica gel (EtOAc:hexane = 1:9) to give the corresponding product.
95% With 6C6H3NO2S(2-)*6Cu(1+)*Cd(2+)*3C2H8N2*10H2O*4H(1+) In dichloromethane at 0℃; for 8h; Inert atmosphere;
81% With C13H10N2O4(2-)*Cd(2+)*2H2O In dichloromethane at 20℃; for 4h; Inert atmosphere;
75% With tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 0.75h; Inert atmosphere; Representative procedure for synthesis of cyanohydrins/cyanohydrin trimethylsilyl ether/α-amino nitriles General procedure: To a stirred solution of carbonyl compound (1.0 mmol)/imine and trimethyl silyl cyanide (1.2 mmol) in dichloromethane (5 ml), was added B(C6F5)3 (3 mol %) under nitrogen atmosphere at room temperature. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water and extracted with mdichloromethane. The organic layer was dried over magnesium sulphate, filtered and evaporated under reduced pressure to give the grude product which was purified by column chromotography over silica gel. The spectroscopic data of the known products were compared with the earlier literature and the data for the new compounds is given below.
66% With CHF3O3S*C23H22BNO In toluene at -40℃; for 16h; Inert atmosphere;
(i) AlCl3, (ii) H2O, Et2O; Multistep reaction;
With copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 25℃;
With [Cu2- (μ3-OH)(H2O){(NO2)-C6H3-(COO) 2}(CN4H)]*(H2O) In dichloromethane at 0℃; for 6h; Inert atmosphere;
In toluene for 0.0833333h; Inert atmosphere;
349 mg With iodine at 20℃; 4.6.1.1 General procedure for the preparation of 2-(2-(benzyloxy)phenyl)-2-(phenylamino) acetonitrile (D2) General procedure: A solution of 2-(benzyloxy)benzaldehyde (1.00g, 4.71mmol) and aniline (438.77mg, 4.71mmol) in acetonitrile (20mL) was stirred at rt for 30min. Then TMSCN (701.13mg, 7.07mmol) and I2 (119.58mg, 0.47mmol) were added and the mixture was stirred overnight. The solvent was evaporated in vacuo and the residual was diluted with ethyl acetate/water. The organic layer was washed with saturated brine, dried over MgSO4 and concentrated under vacuum. The residual was triturated with ethyl acetate/hexane (1/6), filtered to give the product, 1.35g, 91% yield.
at 20℃; for 2h;
99 %Spectr. With chromium doped aluminoborate PKU-3 In dichloromethane at 20℃; for 3h;
95 %Chromat. With [Cu3(hbpdc)(OH)2(H2O)]*2H2O}n In dichloromethane at 24.84℃; for 4h; Inert atmosphere;
With 2C9H5N2O4(1-)*In(3+)*Cl(1-)*H2O In chloroform-d1 at 20℃; for 168h; 2.4 Catalytic experiment General procedure: Samples of 1 and 2 were activated at 200°C for 12h, soaked in CH3OH for 24h and then heated under vacuum at 80°C for 12h under vacuum before the reaction. The basic framework of 1 and 2 are retained after activation. For the experiments of catalysis, activated catalyst (0.04mmol), aldimine (0.14mmol) and TMSCN (47μl) in CDCl3 (2.4l) were sequentially added to a standard 20l vial. The reaction mixtures were stirred at room temperature. The reactions were monitored by 1H NMR spectroscopy and the conversion yield was determined from the ratio of the integral of the product signal in relation to the sum of integrals of all signals (aldimine and product).
With 4C8H3NO6(2-)*H(1+)*3In(3+)*2HO(1-) In chloroform-d1 at 20℃; for 24h; General procedure: Sample 1 was soaked in CH3OH for 24h at room temperature and then heated at 100°C for 12h under vacuum before the reaction to remove guest molecules from pores and surface. The basic framework of 1 was retained after activation. For the catalytic experiments, activated catalyst (0.0134mmol), aldimine (0.14mmol) and trimethylsilyl cyanide (TMSCN) (47μl) in CDCl3 (2.4ml) were sequentially added to a glass vial of 20ml. The reaction mixtures were stirred at room temperature. The reactions were monitored by 1H NMR spectroscopy and conversion yield was determined from the ratio of the integral of the product signal in relation to the sum of integrals of all signals (aldehyde, aldimine and products).
With poly[Ag8(SO4)4(melamine)3] at 0℃; for 2h;
With poly[Ag8(SO4)4(melamine)3] at 0℃; for 2h;
With C8H5NO4(2-)*Sc(3+)*HO(1-)*H2O In chloroform-d1 at 20℃; for 12h;
With C13H10N2O4(2-)*3H2O*Cu(2+) In dichloromethane at 20℃; for 5h; Inert atmosphere;
88 %Spectr. With (H3O)[Cd(II)(4-(3,5-dicarboxylphenyl)picolinate)] metal-organic framework/poly(vinylidene fluoride) mixed-matrix membrane In [D3]acetonitrile at 20℃; for 24h;

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[5]Sarkar, Anupam; Jana, Ajay Kumar; Natarajan, Srinivasan [New Journal of Chemistry, 2021, vol. 45, # 14, p. 6503 - 6511]
[6]Kumar, Nikhil; Paul, Avijit Kumar [Inorganic Chemistry, 2020, vol. 59, # 2, p. 1284 - 1294]
[7]Bolles, Amanda K.; Fujiwara, Rina; Briggs, Erran D.; Nomeir, Amin A.; Furge, Laura Lowe [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53B, # 11, p. 1471 - 1475]
[8]Kang, Ki-Tae; Park, Sang Hyun; Ryu, Do Hyun [Organic Letters, 2019, vol. 21, # 17, p. 6679 - 6683]
[9]Ojima,I. et al. [Chemistry Letters, 1975, p. 331 - 334]
[10]Paraskar, Abhimanyu S.; Sudalai, Arumugam [Tetrahedron Letters, 2006, vol. 47, # 32, p. 5759 - 5762]
[11]Location in patent: experimental part Sarma, Debajit; Ramanujachary; Stock, Norbert; Natarajan, Srinivasan [Crystal Growth and Design, 2011, vol. 11, # 4, p. 1357 - 1369]
[12]Gualtierotti, Jean-Baptiste; Schumacher, Xavier; Wang, Qian; Zhu, Jieping [Synthesis, 2013, vol. 45, # 10, p. 1380 - 1386]
[13]Deng, Xiaodong; Lin, Fu; Zhang, Ya; Li, Yan; Zhou, Lu; Lou, Bin; Li, Yue; Dong, Jibin; Ding, Tingbo; Jiang, Xiancheng; Wang, Renxiao; Ye, Deyong [European Journal of Medicinal Chemistry, 2014, vol. 73, p. 1 - 7]
[14]Su, Chenliang; Tandiana, Rika; Balapanuru, Janardhan; Tang, Wei; Pareek, Kapil; Nai, Chang Tai; Hayashi, Tamio; Loh, Kian Ping [Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 685 - 690]
[15]Chen, Hong; Ju, Jing; Meng, Qingpeng; Su, Jie; Lin, Cong; Zhou, Zhengyang; Li, Guobao; Wang, Weilu; Gao, Wenliang; Zeng, Chunmei; Tang, Chiu; Lin, Jianhua; Yang, Tao; Sun, Junliang [Journal of the American Chemical Society, 2015, vol. 137, # 22, p. 7047 - 7050]
[16]Deng, Dongsheng; Guo, Hui; Kang, Guohui; Ma, Lufang; He, Xu; Ji, Baoming [CrystEngComm, 2015, vol. 17, # 8, p. 1871 - 1880]
[17]Chai, Juan; Wang, Pengcheng; Jia, Jia; Ma, Bing; Sun, Jing; Tao, Yufang; Zhang, Ping; Wang, Li; Fan, Yong [Polyhedron, 2018, vol. 141, p. 369 - 376]
[18]Chai, Juan; Zhang, Ping; Xu, Jianing; Qi, Hui; Sun, Jing; Jing, Shubo; Chen, Xiaodong; Fan, Yong; Wang, Li [Inorganica Chimica Acta, 2018, vol. 479, p. 165 - 171]
[19]Paul, Avijit Kumar; Naveen, Kumari; Kumar, Nikhil; Kanagaraj, Rajendiran; Vidya; Rom, Tanmay [Crystal Growth and Design, 2018, vol. 18, # 11, p. 6411 - 6416]
[20]Paul, Avijit Kumar; Naveen, Kumari; Kumar, Nikhil; Kanagaraj, Rajendiran; Vidya; Rom, Tanmay [Crystal Growth and Design, 2018]
[21]Chai, Juan; Zhang, Ping; Shi, Xiangxiang; Sun, Jing; Wang, Li; Fan, Yong [CrystEngComm, 2019, vol. 21, # 36, p. 5440 - 5447]
[22]Kumar, Nikhil; Rom, Tanmay; Singh, Virender; Paul, Avijit Kumar [Crystal Growth and Design, 2020, vol. 20, # 8, p. 5277 - 5288]
[23]Jiang, Yansong; Sun, Jing; Yang, Xiaona; Shen, Jieyu; Fu, Yu; Fan, Yong; Xu, Jianing; Wang, Li [Inorganic Chemistry, 2021, vol. 60, # 3, p. 2087 - 2096]
  • 16
  • [ 581-40-8 ]
  • [ 538-51-2 ]
  • [ 72160-80-6 ]
YieldReaction ConditionsOperation in experiment
51% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90 - 95℃; for 1h;
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide
  • 17
  • [ 613-33-2 ]
  • [ 538-51-2 ]
  • [ 79567-15-0 ]
  • 18
  • [ 581-42-0 ]
  • [ 538-51-2 ]
  • [ 80236-22-2 ]
YieldReaction ConditionsOperation in experiment
71% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 90 - 95℃; for 1h;
With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide
  • 19
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  • 20
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  • [ 762-04-9 ]
  • diethyl[anilino(phenyl)methyl]phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With C42H74LiN6Si4Yb In tetrahydrofuran at 40℃; for 6h; Inert atmosphere;
93% In neat (no solvent) at 80℃; for 0.166667h; Microwave irradiation; Sealed tube; General procedure for the synthesis of the α-aminophosphonates and α-aminophosphineoxides General procedure: A mixture of 1 mmol imine derivate [1a (0.16 g), 1b (0.19 g), 1c (0.18 g), 1d-e (0.20 g)] and>P(O)H derivative (1.0 mmol [dimethyl phosphite (0.092 mL), diethyl phosphite (0.13 mL)] or1.2 mmol [dimethyl phosphite (0.11 mL), diethyl phosphite (0.15 mL), dibutyl phosphite(0.23 mL), dibenzyl phosphite (0.27 mL), diphenylphosphine oxide (0.24 g)] or 1.5 mmol[dimethyl phosphite (0.14 mL)]) was irradiated in a sealed tube at 80-100 °C for 10-60 min in aCEM Microwave reactor equipped with a pressure controller. The volatile components wereremoved under reduced pressure. The residue obtained was purified by flash columnchromatography using silica gel and dichloromethane/methanol 97:3 or ethyl acetate/hexane 1:1as the eluent to afford α-aminophosphonates and α-aminophosphine oxides.
87% With dioxomolybdenum(VI) dichloride at 80℃; for 0.25h; Inert atmosphere; Neat (no solvent); chemoselective reaction;
85% With potassium fluoride on basic alumina at 20℃; for 24h;
85% With formic acid In ethanol at 20℃; for 3h; Green chemistry; General procedure for synthesisof α-aminophosphonates General procedure: Aqueous formic acid-ethanol solution was prepared from1 ml formic acid (37%) and 4 ml ethanol (final concentration of formic acid is about 7%). Aldehyde (1.0 mmol) and aniline(1.1 mmol) was added to aqueous formic acid-ethanolsolution at room temperature and after 5 min dialkyl phosphite(1.1 mmol) was added to the mixture. After completionthe reaction, solvents were evaporated under reducedpressure. Water was added to the reaction mixture and theresulting solution was neutralized by sodium bicarbonate.The reaction product was extracted with dichloromethane.The crude mixture was purified by chromatography(hexane:ethylacetate; 3:1) to afford pure products.
84% at 90℃; for 8h;
83% With p-toluenesulfonyl chloride In dichloromethane at 20℃; for 2h;
79% With tetra-(n-butyl)ammonium iodide; potassium carbonate In benzene at 40 - 45℃; for 5h;
75% In benzene at 40 - 45℃; for 1.5h;
74% With samarium diiodide; 4 Angstroem MS In acetonitrile at 80℃; for 24h;
In benzene Heating; Yield given;
220 mg In toluene at 100℃; for 24h; Green chemistry; General procedure for the synthesis of α-aminophosphonates (4) from the one-pot three-component condensation of alcohols, amines, and diethylphosphite General procedure: To a mixture of CuO(at)Fe3O4 nanoparticles (40 mg, 1.3 mol % based on copper) and NaOH (1.4 mmol, 56 mg) in toluene (3 mL), alcohol (1 mmol) and amine (2 mmol) were added, and the mixture was stirred at 100 °C for 4 days in an open flask. Diethylphosphite (1 mmol, 0.13 ml) was added to the reaction mixture, and the mixture was stirred for 24-48 h (see Table 2) at 100 °C. The reaction progress was monitored by TLC until the completion of the reaction. After cooling, EtOAc (5 mL) was added to the reaction mixture, and the catalyst was separated by an external magnet, washed thoroughly with methanol and distilled water and dried at 90 °C for 3 h for the next reaction. Then, the product was extracted by EtOAc (3 x 10 mL). The combined organic phases were concentrated. The residue was purified with column chromatography to give α-aminophosphonate 4 in 57-72% isolated yield. All α-aminophosphonate 4 gave satisfactory spectral data in accord with the assigned structures and literature reports. O,O'-Diethyl [(anilino)phenylmethyl] phosphonate (4a) White solid (70%, 220 mg); mp: 91-93 °C [Lit [45]. 90-92 °C]; 1H NMR (400 MHz, CDCl3): δ (ppm) 1.15 (t, 3H, J = 7.2 Hz), 1.32 (t, 3H, J = 7.2 Hz), 3.67-3.74 (m, 1H), 3.94-4.00 (m,1H), 4.12-4.19 (m, 2H), 4.81 (d, 2H, br, NH + CHP JPH = 24.0 Hz), 6.65(d, 2H, J = 8.0 Hz), 6.73 (t, 1H, J = 7.6 Hz), 7.14 (t, 2H, J = 7.6 Hz), 7.28-7.31 (m, 1H), 7.36 (t, 2H, J = 7.6 Hz), 7.52 (d, 2H, J = 7.2 Hz) 13C NMR (100 MHz, CDCl3): δ (ppm) 16.2 (d, JPC = 6.0 Hz), 16.4 (d, JPC = 6.0 Hz), 55.6 (d, JPC = 150.0 Hz), 63.2 (d, JPC = 7.0 Hz) 63.3 (d, JPC = 7.0 Hz), 114.0, 118.5, 127.9, 127.9 (d, JPC = 4.0 Hz), 128.6 (d, JPC = 3.0 Hz), 129.20, 135.82 (d, JPC = 3.0 Hz), 146.19 (d, JPC = 15.0 Hz) 31P NMR (162 MHz, CDCl3/H3PO4): δ (ppm) 22.59.

Reference: [1]Location in patent: experimental part Zhu, Xiancui; Wang, Shaowu; Zhou, Shuangliu; Wei, Yun; Zhang, Lijun; Wang, Fenhua; Feng, Zhijun; Guo, Liping; Mu, Xiaolong [Inorganic Chemistry, 2012, vol. 51, # 13, p. 7134 - 7143]
[2]Bálint, Erika; Tajti, Ádám; Ádám, Anna; Csontos, István; Karaghiosoff, Konstantin; Czugler, Mátyás; Ábrányi-Balogh, Péter; Keglevich, György [Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 76 - 86]
[3]Location in patent: experimental part De Noronha, Rita G.; Romão, Carlos C.; Fernandes, Ana C. [Catalysis Communications, 2011, vol. 12, # 5, p. 337 - 340]
[4]Villemin, Didier; Racha, Rassem [Tetrahedron Letters, 1986, vol. 27, # 16, p. 1789 - 1790]
[5]Azarnia Mehraban, Jamshid; Jalali, Mahsa Sadat; Heydari, Akbar [Chemical Papers, 2018, vol. 72, # 9, p. 2215 - 2223]
[6]Su, Chenliang; Tandiana, Rika; Balapanuru, Janardhan; Tang, Wei; Pareek, Kapil; Nai, Chang Tai; Hayashi, Tamio; Loh, Kian Ping [Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 685 - 690]
[7]Location in patent: experimental part Kaboudin, Babak; Jafari, Elaheh [Synlett, 2008, # 12, p. 1837 - 1839]
[8]Kabachnik; Ternovskaya; Zobnina; Beletskaya [Russian Journal of Organic Chemistry, 2002, vol. 38, # 4, p. 484 - 486]
[9]Kabachnik; Ternovskaya; Zobnina; Beletskaya [Russian Journal of Organic Chemistry, 2002, vol. 38, # 4, p. 480 - 483]
[10]Xu, Fan; Luo, Yiqin; Deng, Mingyu; Shen, Qi [European Journal of Organic Chemistry, 2003, # 24, p. 4728 - 4730]
[11]Jagodic,V. [Chemische Berichte, 1960, vol. 93, p. 2308 - 2313]
[12]Ha; Nam [Synthetic Communications, 1992, vol. 22, # 8, p. 1143 - 1148]
[13]Kaboudin, Babak; Kazemi, Foad; Hosseini, Narges Kadkhoda [Research on Chemical Intermediates, 2017, vol. 43, # 8, p. 4475 - 4486]
  • 21
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  • [ 100-52-7 ]
  • 24
  • [ 3511-34-0 ]
  • [ 538-51-2 ]
  • [ 77147-98-9 ]
YieldReaction ConditionsOperation in experiment
72% In acetic acid for 3h; Ambient temperature;
  • 26
  • [ 4706-43-8 ]
  • [ 538-51-2 ]
  • [ 95-14-7 ]
  • [ 62-53-3 ]
  • [ 501-65-5 ]
  • 28
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  • [ 142819-59-8 ]
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  • [ 501-65-5 ]
  • 30
  • [ 50427-77-5 ]
  • [ 538-51-2 ]
  • [ 130925-67-6 ]
YieldReaction ConditionsOperation in experiment
74% In acetic acid for 4h; Heating;
  • 31
  • [ 758640-21-0 ]
  • [ 538-51-2 ]
  • [ 100-52-7 ]
YieldReaction ConditionsOperation in experiment
94% With tert.-butylhydroperoxide In acetonitrile at 20℃; for 16h; 7.7 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
1: 11% 2: 84% With oxygen In ethanol at 60℃; for 24h;
1: 94 % Spectr. 2: 6 % Spectr. With tert.-butylhydroperoxide In dimethyl sulfoxide at 40℃; for 8h;
With oxygen In ethanol at 60℃; for 24h; different Co(II) Schiff base complexes were used as catalyst;
With oxygen at 60℃; for 24h; in different solvents;
1: 94 % Spectr. 2: 6 % Spectr. With tert.-butylhydroperoxide In dimethyl sulfoxide at 40℃; for 8h; deuterium isotope effect, other educts, other cobalt schiff base catalysts, also with Co(III)(L1)(OOtBu);
With tert.-butylhydroperoxide; sodium hydrogencarbonate In dichloromethane at 20℃; for 16h; 7.1 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
With tert.-butylhydroperoxide; magnesium sulfate In dichloromethane at 20℃; for 16h; 7.4 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
With tert.-butylhydroperoxide In dichloromethane at 20℃; for 16h; Molecular sieve; 7.3 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
With tert.-butylhydroperoxide In dichloromethane at 20℃; for 16h; 7.2 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
With tert.-butylhydroperoxide In methanol at 20℃; for 16h; 7.5 Example 7 Oxidation of Secondary AminesRh2(cap)4/tert-Butyl hydroperoxide can be used under anhydrous conditions to mediate the oxidation of secondary amine, as shown below: N-Phenylbenzylamine (1) was selected to determine suitable conditions for oxidation with TBHP catalyzed by Rh2(cap)4 at 1.0 mol % catalyst loading (Table 1). Previously described conditions for benzylic oxidation (entry 1)9b gave complete conversion of 1, but benzylidineaniline (2) was accompanied by its hydrolysis product benzaldehyde (3). Benzaldehyde formation with complete substrate conversion was diminished in the absence of NaHCO3 (entry 2). Attempts to decrease the extent of hydrolysis even further using molecular sieves or anhydrous MgSO4 were unsuccessful (entries 3 and 4) because they significantly limited the oxidation of 1. Methanol, the solvent of choice for the oxidation of N-aryl tertiary amines,10 was found be effective (entry 5); however, when N-cyclohexylbenzylamine was submitted to reaction under the same conditions, no imine product was obtained at room temperature (entry 6), and only trace amounts were obtained at temperatures up to 60° C. However, the use of acetonitrile as the solvent gave optimal results for both N-phenyl- and N-cyclohexylbenzylamine substrates (entries 7 and 8) with quantitative conversion, chromatographically pure product in high yield, and the absence of hydrolysis. We assume that steric effects in the two solvents are responsible for the difference in reaction outcomes (entries 6 and 8).
With tert.-butylhydroperoxide In decane; acetonitrile at 60℃; for 1.5h;

Reference: [1]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[2]Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo [Tetrahedron Letters, 1988, vol. 29, # 33, p. 4115 - 4118]
[3]Maruyama, Kazushige; Kusukawa, Takahiro; Higuchi, Yoshihiko; Nishinaga, Akira [Chemistry Letters, 1991, # 7, p. 1093 - 1096]
[4]Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo [Tetrahedron Letters, 1988, vol. 29, # 33, p. 4115 - 4118]
[5]Nishinaga, Akira; Yamazaki, Shigekazu; Matsuura, Teruo [Tetrahedron Letters, 1988, vol. 29, # 33, p. 4115 - 4118]
[6]Maruyama, Kazushige; Kusukawa, Takahiro; Higuchi, Yoshihiko; Nishinaga, Akira [Chemistry Letters, 1991, # 7, p. 1093 - 1096]
[7]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[8]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[9]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[10]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[11]Current Patent Assignee: UNIVERSITY SYSTEM OF MARYLAND - US2009/93638, 2009, A1 Location in patent: Page/Page column 24-25
[12]Location in patent: experimental part Khatri, Praveen K.; Jain, Suman L.; Sivakumar K.; Sain, Bir [Organic and Biomolecular Chemistry, 2011, vol. 9, # 9, p. 3370 - 3374]
  • 32
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  • [ 134414-85-0 ]
  • 33
  • [ 91-44-1 ]
  • [ 538-51-2 ]
  • [ 136886-34-5 ]
YieldReaction ConditionsOperation in experiment
48% With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 40 - 45℃; for 2h;
  • 34
  • [ 108-24-7 ]
  • [ 538-51-2 ]
  • [ 6840-29-5 ]
YieldReaction ConditionsOperation in experiment
80% With triethylsilane; zinc In tetrahydrofuran at 20℃; for 0.75h; General procedure for the preparation of amide 3 General procedure: A mixture of imine (1 mmol), anhydride (2 mmol), Et3SiH (4 mmol), and activated Zn dust (1.2 mmol) in THF (5 mL) was stirred at room temperature for 45 min (the progress of the reaction was monitored by TLC). After completion of the reaction, the mixture was filtered, and H2O (20 mL) was added to the filtrate which was extracted with CH2Cl2 (3 × 5 mL). The combined organic layer was dried over anhydrous MgSO4 and concentrated by rotary evaporation. The residue was purified by flash column chromatography (EtOAc/petroleum ether).
58.6% With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane for 6h; or with acetyl chloride;
  • 35
  • [ 56-23-5 ]
  • [ 538-51-2 ]
  • [ 3543-98-4 ]
YieldReaction ConditionsOperation in experiment
96% With magnesium In tetrahydrofuran for 0.2h; Sonication; 2.3 General procedure for the synthesis of 2,2-dichloro-1,3-diphenylaziridines A mixture of magnesium powder (80mmol), Schiff base compounds 1a (40 mmol) and CCl4 (80mmol) in anhydrous tetrahydrofuran (8mL) was placed in flask equipped with ultrasonic prob. The mixture was then treated with ultrasonic irradiation until all magnesium was consumed. To the reaction mixture was then added 10% NH4Cl solution (30 mL) and the aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and desired product, gem-dichloroaziridine, was obtained in excellent yield. All of the diarylaziridine products were identified by physical and spectroscopic data as following and were consistent in comparison with authentic samples [34,36-38].
80 % Turnov. With cyclohexene In chloroform at 15 - 20℃; for 5h; electrolysis on Pb cathode, Pt anode, galvanostatic regime I 0.15-0.2 A, Et4NBr supporting electrolyte;
  • 36
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  • [ 125112-28-9 ]
  • 37
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  • [ 538-51-2 ]
  • [ 606-87-1 ]
  • [ 135505-50-9 ]
YieldReaction ConditionsOperation in experiment
22% With sodium; N,N-dimethyl-formamide at 30℃; for 24h; Yields of byproduct given;
  • 38
  • [ 683-98-7 ]
  • [ 538-51-2 ]
  • [ 120316-02-1 ]
YieldReaction ConditionsOperation in experiment
87% With zinc In tetrahydrofuran Heating;
  • 39
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YieldReaction ConditionsOperation in experiment
36% With sodium; N,N-dimethyl-formamide at 75℃; for 0.5h;
  • 41
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  • [ 3684-12-6 ]
  • 42
  • [ 70591-20-7 ]
  • [ 538-51-2 ]
  • [ 139616-33-4 ]
  • 43
  • [ 946-80-5 ]
  • [ 538-51-2 ]
  • [ 606-87-1 ]
YieldReaction ConditionsOperation in experiment
100% With sodium In N,N-dimethyl-formamide
73% With sodium; N,N-dimethyl-formamide at 75℃; for 0.5h; variation of stoichiometry, addition of aniline; other (arylmethoxy)arenes;
73% With sodium; N,N-dimethyl-formamide at 75℃; for 0.5h;
  • 44
  • [ 606-87-1 ]
  • [ 538-51-2 ]
  • [ 134414-84-9 ]
YieldReaction ConditionsOperation in experiment
75% In N,N-dimethyl-formamide at 75℃; for 2.5h;
  • 45
  • [ 72633-22-8 ]
  • [ 538-51-2 ]
  • [ 606-87-1 ]
  • [ 65181-77-3 ]
YieldReaction ConditionsOperation in experiment
1: 14% 2: 20% With sodium; N,N-dimethyl-formamide at 100℃; for 1h;
  • 46
  • [ 7700-27-8 ]
  • [ 538-51-2 ]
  • [ 606-87-1 ]
  • [ 57003-80-2 ]
YieldReaction ConditionsOperation in experiment
17% With sodium; N,N-dimethyl-formamide at 50℃; for 7h; Yields of byproduct given;
  • 47
  • [ 3762-25-2 ]
  • [ 538-51-2 ]
  • diethyl ester of (erythro)-2-phenylamino-2-phenyl-1-(4-methylphenyl)-ethanephosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With lithium amide In diethyl ether at -33℃; for 6h;
  • 48
  • [ 3762-25-2 ]
  • [ 538-51-2 ]
  • diethyl ester of (threo)-2-phenylamino-2-phenyl-1-(4-methylphenyl)-ethanephosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With sodium amide In N,N,N,N,N,N-hexamethylphosphoric triamide at 10℃; for 1.25h;
  • 49
  • [ 77385-90-1 ]
  • [ 538-51-2 ]
  • (3R,4S)-3-Dibenzylamino-1,4-diphenyl-azetidin-2-one [ No CAS ]
  • (3S,4S)-3-Dibenzylamino-1,4-diphenyl-azetidin-2-one [ No CAS ]
  • 50
  • [ 538-51-2 ]
  • [ 21911-75-1 ]
  • [ 120638-33-7 ]
  • 51
  • [ 75-77-4 ]
  • [ 538-51-2 ]
  • [ 100-52-7 ]
  • [ 82940-37-2 ]
  • (1,2-Diphenyl-2-trimethylsilanyloxy-ethyl)-phenyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetraethylammonium tosylate; triethylamine In N,N-dimethyl-formamide electrolysis;
  • 52
  • [ 538-51-2 ]
  • [ 100-52-7 ]
  • [ 758640-21-0 ]
  • [ 82940-37-2 ]
YieldReaction ConditionsOperation in experiment
1: 40% 2: 32% With naphthalene; lithium In tetrahydrofuran at -78 - 20℃; for 5h;
  • 53
  • [ 538-51-2 ]
  • [ 100-52-7 ]
  • [ 82940-37-2 ]
  • (1,2-Diphenyl-2-trimethylsilanyloxy-ethyl)-phenyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloro-trimethyl-silane; water; tetraethylammonium tosylate; triethylamine 1) DMF, electrolysis; Yield given. Multistep reaction;
  • 54
  • [ 538-51-2 ]
  • [ 68-11-1 ]
  • [ 29291-15-4 ]
YieldReaction ConditionsOperation in experiment
97% With copper(ll) sulfate pentahydrate In toluene at 110℃; for 12h; Green chemistry; regioselective reaction; A mixture of ligand L3 (0.005g, 0.01mmol) and CuSO4·5H2O (0.001g, 0.05mmol) in toluene (0.5mL) was stirred magnetically and then heated for 0.5h at 110°C reflux. Then, imine (0.018g, 0.1mmol) and mercaptoacetic acid (0.014g, 0.15mmol) were added. The progress of the reaction was monitored by TLC using ethyl acetate/petroleum ether (1/10-1/5). Upon completion of the reaction, the crude mixture was purified by column chromatography on silica gel (ethyl acetate/petroleum ether) to afford the desired pure product (3a) in 97% yield.
65% With piperidine In ethanol for 2h; Heating;
60% In toluene Heating;
With toluene-4-sulfonic acid In chloroform; acetic acid at 30℃;
With N-methylpyridinium p-toluenesulfonate at 120℃; for 1h;
In benzene for 8h; Reflux;

  • 56
  • [ 538-51-2 ]
  • [ 5334-31-6 ]
  • 5-[1-Phenyl-meth-(E)-ylidene]-amino}-1H-pyrazole-4-carboxylic acid amide [ No CAS ]
  • 57
  • [ 538-51-2 ]
  • [ 184297-69-6 ]
  • [ 111508-24-8 ]
YieldReaction ConditionsOperation in experiment
44% With potassium <i>tert</i>-butylate 1.) THF, -10 deg C, 10 min, 2.) THF, 25 deg C, 18 h;
  • 58
  • [ 538-51-2 ]
  • [ 184297-69-6 ]
  • [ 142819-60-1 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide 1.) cyclohexane, THF, -78 deg C, 15 min, 2.) THF, -78 deg C -> 25 deg C, 4 h; Yield given. Multistep reaction;
  • 59
  • [ 538-51-2 ]
  • [ 106-95-6 ]
  • [ 66489-79-0 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: allyl bromide With indium; 1-butylpyridinium bromide; N-butylpyridinium tetrafluoroborate at 20℃; for 1h; Stage #2: benzylidene phenylamine at 20℃; for 12h;
95% With samarium diiodide In tetrahydrofuran at 20℃; for 6h;
94% Stage #1: benzylidene phenylamine; allyl bromide With gallium for 12h; sonication; Stage #2: With water for 0.25h; sonication; Further stages.;
92% With ammonium bromide In tetrahydrofuran; water at 20℃; for 1.25h; Electrochemical reaction; zinc electrodes;
91% With zinc at 20℃; neat (no solvent);
90% With tetrabutylammomium bromide; cadmium In tetrahydrofuran for 4h; Ambient temperature;
88% With bis(pinacol)diborane; copper(l) chloride; lithium tert-butoxide In 1,4-dioxane at 80℃; for 18h;
86% Stage #1: allyl bromide With chloro-trimethyl-silane; ethylene dibromide; zinc In tetrahydrofuran at 20 - 70℃; Inert atmosphere; Stage #2: benzylidene phenylamine at 20℃; for 0.0833333h; neat (no solvent); regioselective reaction;
75% With chloro-trimethyl-silane; ytterbium In tetrahydrofuran at 20℃;
46% With zinc In dimethyl sulfoxide for 2h; Milling;
With indium 1.) dioxane, RT, 40 min, 2.) dioxane, RT, 24 h; Yield given. Multistep reaction;
With magnesium In diethyl ether at 10℃;
With bis(cyclopentadienyl)-titanium(III) chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Stage #1: benzylidene phenylamine; allyl bromide With chromium chloride; manganese; chloro-trimethyl-silane In tetrahydrofuran; N,N-dimethyl-formamide for 16h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.166667h;

Reference: [1]Man, Chun Law; Tin, Wai Cheung; Wong, Kwok-Yin; Tak, Hang Chan [Journal of Organic Chemistry, 2007, vol. 72, # 3, p. 923 - 929]
[2]Kim, Byeong Hyo; Han, Rongbi; Park, Ryun Ju; Bai, Kyung Ho; Jun, Young Moo; Baik, Woonphil [Synthetic Communications, 2001, vol. 31, # 15, p. 2297 - 2304]
[3]Andrews, Philip C.; Peatt, Anna C.; Raston, Colin L. [Tetrahedron Letters, 2004, vol. 45, # 2, p. 243 - 248]
[4]Location in patent: experimental part Huang, Jing-Mei; Wang, Xu-Xiao; Dong, Yi [Angewandte Chemie - International Edition, 2011, vol. 50, # 4, p. 924 - 927]
[5]Zhang, Yumei; Yan, Tingli; Cheng, Wei; Zuo, Jianming; Zhao, Weijie [Tetrahedron Letters, 2009, vol. 50, # 24, p. 2925 - 2928]
[6]Sain, Bir; Prajapati, Dipak; Sandhu, Jagir S. [Tetrahedron Letters, 1992, vol. 33, # 33, p. 4795 - 4798]
[7]Li, Zhenghua; Zhang, Liang; Nishiura, Masayoshi; Hou, Zhaomin [ACS Catalysis, 2019, p. 4388 - 4393]
[8]Location in patent: experimental part Zhang, Yumei; Han, Minghu; Yan, Tingli [Synthetic Communications, 2012, vol. 42, # 18, p. 2689 - 2693]
[9]Su; Li; Zhang [Synthetic Communications, 2001, vol. 31, # 2, p. 273 - 277]
[10]Yin, JieXiang; Stark, Roderick T.; Fallis, Ian A.; Browne, Duncan L. [Journal of Organic Chemistry, 2020, vol. 85, # 4, p. 2347 - 2354]
[11]Jin, Shun-Ji; Araki, Shuki; Butsugan, Yasuo [Bulletin of the Chemical Society of Japan, 1993, vol. 66, # 5, p. 1528 - 1532]
[12]Kouznetsov; Urbina; Palma; Lopez; Devia; Enriz; Zacchino [Molecules, 2000, vol. 5, # 3, p. 428 - 430]
[13]Location in patent: experimental part Saha, Sumit; Roy, Subhas Chandra [Journal of Organic Chemistry, 2011, vol. 76, # 17, p. 7229 - 7234]
[14]Location in patent: scheme or table Durán-Galván, María; Connell, Brian T. [Tetrahedron, 2011, vol. 67, # 41, p. 7901 - 7908]
  • 60
  • [ 6245-96-1 ]
  • [ 538-51-2 ]
  • [ 33513-42-7 ]
  • [ 606-87-1 ]
  • 1-styrylnaphthalene [ No CAS ]
  • [ 135505-51-0 ]
  • [ 93018-96-3 ]
YieldReaction ConditionsOperation in experiment
42% With sodium at 75℃; for 0.5h;
  • 61
  • [ 538-51-2 ]
  • [ 868-85-9 ]
  • [ 26624-91-9 ]
YieldReaction ConditionsOperation in experiment
92% In neat (no solvent) at 80℃; for 0.166667h; Microwave irradiation; Sealed tube; General procedure for the synthesis of the α-aminophosphonates and α-aminophosphineoxides General procedure: A mixture of 1 mmol imine derivate [1a (0.16 g), 1b (0.19 g), 1c (0.18 g), 1d-e (0.20 g)] and>P(O)H derivative (1.0 mmol [dimethyl phosphite (0.092 mL), diethyl phosphite (0.13 mL)] or1.2 mmol [dimethyl phosphite (0.11 mL), diethyl phosphite (0.15 mL), dibutyl phosphite(0.23 mL), dibenzyl phosphite (0.27 mL), diphenylphosphine oxide (0.24 g)] or 1.5 mmol[dimethyl phosphite (0.14 mL)]) was irradiated in a sealed tube at 80-100 °C for 10-60 min in aCEM Microwave reactor equipped with a pressure controller. The volatile components wereremoved under reduced pressure. The residue obtained was purified by flash columnchromatography using silica gel and dichloromethane/methanol 97:3 or ethyl acetate/hexane 1:1as the eluent to afford α-aminophosphonates and α-aminophosphine oxides.
90% With formic acid In ethanol at 20℃; for 3h; Green chemistry; General procedure for synthesisof α-aminophosphonates General procedure: Aqueous formic acid-ethanol solution was prepared from1 ml formic acid (37%) and 4 ml ethanol (final concentration of formic acid is about 7%). Aldehyde (1.0 mmol) and aniline(1.1 mmol) was added to aqueous formic acid-ethanolsolution at room temperature and after 5 min dialkyl phosphite(1.1 mmol) was added to the mixture. After completionthe reaction, solvents were evaporated under reducedpressure. Water was added to the reaction mixture and theresulting solution was neutralized by sodium bicarbonate.The reaction product was extracted with dichloromethane.The crude mixture was purified by chromatography(hexane:ethylacetate; 3:1) to afford pure products.
73% With 1,1,3,3-tetramethylguanidine for 2h; Ambient temperature;
In toluene for 1h; Heating;

  • 62
  • [ 538-51-2 ]
  • [ 75-05-8 ]
  • [ 1885-38-7 ]
  • [ 33328-81-3 ]
  • [ 62-53-3 ]
  • [ 100-51-6 ]
  • 63
  • [ 538-51-2 ]
  • [ 122-59-8 ]
  • (±)-cis-3-phenoxy-1,4-diphenyl-2-azetindione [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With triethylamine; N-tosylimidazole In dichloromethane at 20℃; Green chemistry; Synthesis of 2-azetidinones (3-13); general procedure General procedure: A mixture of Schiff base (1.0 mmol), triethylamine (5.0 mmol),carboxylic acid (1.3 mmol) and tosylimidazole (1.3 mmol) in dry CH2Cl2 (20 mL) was stirred at room temperature overnight. The mixture was washed successively with saturated NaHCO3 (20 mL) and brine (15 mL). The organic layer wasdried and the solvent was removed to give the crude product,which was purified by crystallisation from EtOH to give pure2-azetidinones 3-13. 3-Phenoxy-1,4-diphenyl-2-azetindione (3): M.p. 190-192 °C (lit.24191-193 °C).
59% With bis-(2,2,2-trichloroethyl)phosphorochloridate; triethylamine In dichloromethane for 48h; Ambient temperature;
  • 64
  • [ 538-51-2 ]
  • [ 758640-21-0 ]
  • [ 82940-37-2 ]
YieldReaction ConditionsOperation in experiment
1: 32% 2: 40% With naphthalene; lithium; benzaldehyde In tetrahydrofuran at -78 - 20℃; for 5h;
  • 66
  • [ 538-51-2 ]
  • [ 758640-21-0 ]
  • [ 100-52-7 ]
  • [ 62-53-3 ]
YieldReaction ConditionsOperation in experiment
1: 7% 2: 16% 3: 71% With aluminum telluride; water In tetrahydrofuran at 0℃; for 2h;
1: 21 %Chromat. 2: 19 %Chromat. 3: 32 %Chromat. With hydrogen In toluene at 100℃; for 4h; Autoclave; 4.3. Typical experiments for hydrogenations General procedure: An autoclave was charged with substrate, catalyst, solvent, anda magnetic stirring bar. The autoclave was purged and filled with H2. After the reaction mixture was stirred, the mixture was filtered by Celite and the filtrate was analyzed by GC.
1: 73 %Chromat. 2: 8 %Chromat. 3: 8 %Chromat. With hydrogen In toluene at 100℃; for 4h; Autoclave; 4.3. Typical experiments for hydrogenations General procedure: An autoclave was charged with substrate, catalyst, solvent, and a magnetic stirring bar. The autoclave was purged and filled with H2. After the reaction mixture was stirred, the mixture was filtered by Celite and the filtrate was analyzed by GC.
  • 67
  • [ 100-52-7 ]
  • [ 98-95-3 ]
  • [ 538-51-2 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In ethanol at 104.84℃; for 8h; Autoclave; Green chemistry; chemoselective reaction;
93% Stage #1: benzaldehyde; nitrobenzene With sodium tetrahydroborate In water at 20℃; for 0.5h; Green chemistry; Stage #2: benzaldehyde In water at 20℃; for 1.16667h; Green chemistry;
93% With 6Zr6O4(OH)4(2+)*6C7H3NO4(2-); isopropyl alcohol for 20h; Irradiation; 4.5. General catalytic photocascade reactions General procedure: In a typical catalytic reaction, 20 mg of MOF, 1 mmol of nitro compound, 1 mmol of aldehyde and 20 mL of iPrOH were put into the 25 mL Teflon-capped quartz tube. Then reaction vessel was closed and placed 15 cm from 200W Hg/Xe lamp irradiation for 20 h, while the stirring rate was set to 900 rpm. After 20 h, an aliquot of the reaction was transferred through a short Celite plug to remove the solids, and injected into GC-MS.
88% With hydrogenchloride; iron In ethanol; water at 65℃; for 1.5h;
83% With hydrogen; triethylamine In water at 120℃; for 20h; Autoclave;
82% With hydrogen; triethylamine at 110℃; for 24h; Autoclave;
71% With carbon monoxide at 100℃;
71 % Chromat. With bis-triphenylphosphine-palladium(II) chloride; carbon monoxide; tin(ll) chloride In 1,4-dioxane at 100℃;
With methanol; 3%Au-3%Pd/Al2O3; water at 134.84℃; Inert atmosphere; Autoclave;
With 1.5% Au/TiO2; hydrogen at 120℃; for 2h;
60 %Chromat. With hydrogen In isopropyl alcohol at 40 - 80℃; for 16h; 2.3. Cascade reaction procedure Catalytic reactions were performed in a reactor (Autoclave Engineers, 100 mL capacity, 1500 RPM). Conversions and selectivities were measured by NMR and gas chromatographic techniques. All hydrogenated products were initially identified by using authentic commercial samples of the expected products. A mixture of the appropriate nitroaromatic (1 mmol) and aldehyde (1 mmol) was introduced into the reactor together with a catalytic amount of Ru-catalyst (0.02 mmol, 2 mol%) and solvent (ethanol or isopropanol, 40 ml). Afterward, the reactor was sealed and air was purged by flushing three times with 1.5 bar of hydrogen. Then, the reaction mixture was stirred, heated at 40 °C, and the reactor was pressurized with H2 at the required pressure. Ones the nitro compound is hydrogenated to amine, the dihydrogen pressure increased until 5 bar and the temperature at 80 °C. The progress of the reaction was monitored by GC. When the hydrogenation reaction was finished, the reactor was depressurized. Finally, the catalysts were filtered and the organic solution was concentrated under vacuum and analyzed by GC-MS.
With styrene; iron; citric acid In water at 40℃; Sonication;
94 %Chromat. With hydrogen In tetrahydrofuran; water at 120℃; for 24h; Autoclave; Green chemistry;
With hydrogen In ethanol at 100℃; for 5h;
With formic acid; hydrogen In toluene at 120℃; for 2h; 2.3.2 The CTH of Nitrobenzene and Benzaldehyde to Imines General procedure: A mixture of nitrobenzene (1 mmol), benzaldehyde(1 mmol), formic acid (10 mmol), catalyst (1.5 mol %metal), solvents (10 mL) and anisole (1 mmol, the internal standard) were charged into a 50 mL three-necked flaskwith a reflux condenser. The resulting mixture was vigorously stirred in a thermostatic oil bath at set temperature.
With hydrogen In methanol at 20℃; for 0.166667h; Sonication;
18.9 %Chromat. With molybdenum (IV) sulfide; hydrogen In ethanol at 60℃; for 2h;
With hydrogen In isopropyl alcohol at 40℃; for 2h; Autoclave;
22 %Chromat. With hydrogen In methanol at 80℃; for 20h;
With hydrogen In ethanol at 80℃; for 12h;
90 %Chromat. With hydrogen In 1,3,5-trimethyl-benzene at 149.84℃; for 12h; Autoclave; Sealed tube; chemoselective reaction; 2.3. Catalytic test The one-pot reaction of benzaldehyde with nitrobenzene was carried out in a high-pressure autoclave with a pressure gauge, a magnetic stirrer, and an oil bath. Typically, Ni3Sn2/TiO2 alloy catalyst (0.10 g),nitrobenzene (1.0 mmol), benzaldehyde (1.0 mmol), naphthalene(0.3 mmol) as an internal standard material, and mesitylene solvent(5.0 mL) were placed into a glass reaction tube and stirred at room temperature for a selected time. After the autoclave was sealed, pure H2 gas was introduced in order to remove air from the system and kept at a desired pressure, and then the reaction system was heated to a given temperature. After the reaction, the reaction mixture was taken out of the reaction system and analyzed by gas chromatography. The products were identified by gas chromatography (GC-8A, Shimadzu, using aflame ionization detector) equipped with a flexible quartz capillary column coated with Silicon OV-17. The conversion and yields of the products were calculated using an internal standard method.
With hydrogen In cyclohexane at 120℃; for 7h; Autoclave; High pressure; chemoselective reaction; Synthesis of imine General procedure: In general, nitrobenzene (0.24 mmol), benzaldehyde(0.96 mmol), cyclohexane (40 mL) and catalyst (20 mg)were added into a 100 mL stainless-steel autoclave batch reactorsequentially. Then, the reactor was purged 3 times with N2 toreplace air in the reactor, purged with H2 twice to replace N2 and then charged with hydrogen pressure to 1.8 MPa. The autoclavewas heated at 120 C. After reaction, the reactive mixture wascooled to room temperature and then filtered into a sample vial.The separated solution was analyzed by using GC-MS and GC.The catalyst was washed with ethanol and dried at 80 C for recyclabilitymeasurement.

Reference: [1]Ren, Ren; Ma, Jiantai [RSC Advances, 2015, vol. 5, # 91, p. 74802 - 74810]
[2]Sobhani, Sara; Chahkamali, Farhad Omarzehi; Sansano, José Miguel [RSC Advances, 2019, vol. 9, # 3, p. 1362 - 1372]
[3]Elkin; Saouma [Inorganica Chimica Acta, 2019, vol. 497]
[4]Korich, Andrew L.; Hughes, Thomas S. [Synlett, 2007, # 16, p. 2602 - 2604]
[5]Bäumler, Christoph; Kempe, Rhett [Chemistry - A European Journal, 2018, vol. 24, # 36, p. 8989 - 8993]
[6]Schwob, Tobias; Kempe, Rhett [Angewandte Chemie - International Edition, 2016, vol. 55, # 48, p. 15175 - 15179][Angew. Chem., 2016, vol. 128, # 48, p. 15400 - 15404,5]
[7]Akazome, Motohiro; Kondo, Teruyuki; Watanabe, Yoshihisa [Journal of Organic Chemistry, 1994, vol. 59, # 12, p. 3375 - 3380]
[8]Akazome, Motohiro; Kondo, Teruyuki; Watanabe, Yoshihisa [Chemistry Letters, 1992, # 5, p. 769 - 772]
[9]Xiang, Yizhi; Meng, Qiangqiang; Li, Xiaonian; Wang, Jianguo [Chemical Communications, 2010, vol. 46, # 32, p. 5918 - 5920]
[10]Location in patent: experimental part Santos, Laura L.; Serna, Pedro; Corma, Avelino [Chemistry - A European Journal, 2009, vol. 15, # 33, p. 8196 - 8203]
[11]Location in patent: experimental part Del Pozo, Carolina; Corma, Avelino; Iglesias, Marta; Sanchez, Felix [Journal of Catalysis, 2012, vol. 291, p. 110 - 116]
[12]Imrich, Hans-Georg; Conrad, Jürgen; Bubrin, Denis; Beifuss, Uwe [Journal of Organic Chemistry, 2015, vol. 80, # 4, p. 2319 - 2332]
[13]Stemmler, Tobias; Surkus, Annette-Enrika; Pohl, Marga-Martina; Junge, Kathrin; Beller, Matthias [ChemSusChem, 2014, vol. 7, # 11, p. 3012 - 3016]
[14]Chen, Gangquan; Gao, Wenbin; Wang, Xuejun; Huo, Hongfei; Li, Wenzhu; Zhang, Le; Li, Rong; Li, Zuixiong [RSC Advances, 2016, vol. 6, # 63, p. 58805 - 58812]
[15]Wang, Xinkui; Qiu, Zhen; Liu, Qinggang; Chen, Xiao; Tao, Shengyang; Shi, Chuan; Pang, Min; Liang, Changhai [Catalysis Letters, 2017, vol. 147, # 2, p. 517 - 524]
[16]Zheng, Deng-Yue; Zhou, Xue-Meng; Mutyala, Suresh; Huang, Xiao-Chun [Chemistry - A European Journal, 2018, vol. 24, # 72, p. 19141 - 19145]
[17]Han, Wenpeng; Wang, Junwei; Li, Xuekuan; Zhou, Ligong; Yang, Ying; Tang, Mingxing; Ge, Hui [Catalysis Communications, 2019, vol. 124, p. 86 - 91]
[18]Gong, Wanbing; Han, Miaomiao; Chen, Chun; Lin, Yue; Wang, Guozhong; Zhang, Haimin; Zhao, Huijun [ChemCatChem, 2020, vol. 12, # 23, p. 5948 - 5958]
[19]Hara, Michikazu; Kai, Sayaka; Kamata, Keigo; Kita, Yusuke; Supriadi Rustad, Lesandre Binti [RSC Advances, 2020, vol. 10, # 54, p. 32296 - 32300]
[20]Li, Bo; Wang, Yanxin; Chi, Quan; Yuan, Ziliang; Liu, Bing; Zhang, Zehui [New Journal of Chemistry, 2021, vol. 45, # 9, p. 4464 - 4471]
[21]Yamanaka, Nobutaka; Hara, Takayoshi; Ichikuni, Nobuyuki; Shimazu, Shogo [Molecular catalysis, 2021, vol. 505]
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  • 68
  • [ 538-51-2 ]
  • [ 57183-82-1 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: benzylidene phenylamine With titanium(IV) isopropylate; cyclopentylmagnesium chloride In diethyl ether at -30℃; for 1.5h; Inert atmosphere; Stage #2: With water-d2 In diethyl ether at -30 - 20℃; for 1h; Inert atmosphere; Deuteration of the TiII-imine complex. To a stirred solution of imine 1a (91 mg, 0.5 mmol) and Ti(OiPr)4 (0.19 mL, 0.65 mmol) in Et2O (5 mL) was added dropwise of c-C5H9MgCl (0.65 mL, 2.0M solution in diethyl ether, 1.3 mmol) at -30 °C. The solution was stirred for 1.5 h at this temperature. Then D2O (0.5 mL) was added, and the mixture was stirred at -30 °C for 0.5 h. The cold-bath was removed, and the reaction mixture was warmed up to room temperature. After stirring for 0.5 h, the mixture was quenched with water and extracted with diethyl ether. The extract was washed separately with water, brine, and dried over anhydrous Na2SO4. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel to afford the desired deuterated N-benzylaniline (90 mg) in 98% yield. The deuterium incorporation is 96%. 1H NMR (400 MHz, CDCl3) δ 3.93 (bs, 1H), 4.24 (s, 1H), 6.58 (d, J = 8.4 Hz, 2H), 6.69 (t, J = 7.2 Hz, 1H), 7.12-7.16 (m, 2H), 7.24-7.34 (m, 5H); 13C NMR (100 MHz, CDCl3) δ 47.84 (t), 112.74, 117.43, 127.13, 127.42, 128.54, 129.18, 139.31, 148.06.
83% With Hantzsch ester-4,4-d2; silica gel In benzene at 25℃; for 3h;
98 %Chromat. With <3-2H1>pentan-3-ol; cis-[RuH(NH3)(PMe3)4]PF6; potassium carbonate for 2h; Inert atmosphere; Reflux;
With ammonia - [(2)H]borane (1/1) In tetrahydrofuran-d8 at 60℃; Inert atmosphere;
With Li(1+)*N(2)H2BH3(1-)=LiN(2)H2BH3 In tetrahydrofuran

  • 69
  • [ 100-39-0 ]
  • [ 538-51-2 ]
  • [ 91-73-6 ]
YieldReaction ConditionsOperation in experiment
87% With 1-Benzyl-1,4-dihydronicotinamide In acetonitrile at 20℃; for 4h; Irradiation;
77% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; phenylsilane; triphenylphosphine In acetonitrile at 80℃; for 16h; Generalprocedurefor[RuCl2(p-cymene)]2 catalyzeddirectreductive N-benzylationofiminesandbenzylbromidederivatives General procedure: [RuCl2(p-cymene)]2 (0.0125 mmol, 7.7mg), imine (0.5 mmol), benzyl bromide derivatives (0.75 mmol), PhSiH3 (0.75 mmol, 92μL) and acetonitrile (0.5 mL) were introduced in a tube under air, equipped with magnetic stirring bar and was stirred at 80 oC. After16 h, theconversionof thereaction was analyzed by gas chromatography. The solvent was then evaporated under vacuum and the desired product was purified by using a silica gel chromatography column and a mixture of petrol ether/ethyl acetate as eluent.
With Bu2SnClH-HMPA 1.) THF, r.t., 2 h, 2.) 60 deg C, 3 h; Yield given. Multistep reaction;
  • 70
  • [ 100-58-3 ]
  • [ 6780-49-0 ]
  • [ 538-51-2 ]
  • 71
  • [ 538-51-2 ]
  • [ 54323-50-1 ]
  • N-<(3-acetyl-(R)-thiazolidin-4-yl)carbonyl>-N,N'-dicyclohexyl urea [ No CAS ]
  • (3R,4S)-5-Acetyl-2,3-diphenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • (3S,4S)-5-Acetyl-2,3-diphenyl-7-thia-2,5-diaza-spiro[3.4]octan-1-one [ No CAS ]
  • 72
  • [ 108-30-5 ]
  • [ 538-51-2 ]
  • [ 102-14-7 ]
YieldReaction ConditionsOperation in experiment
With acetylacetone In acetic acid; benzene
  • 74
  • [ 538-51-2 ]
  • [ 105-56-6 ]
  • [ 2169-69-9 ]
YieldReaction ConditionsOperation in experiment
82% With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature;
  • 75
  • [ 1212-53-9 ]
  • [ 538-51-2 ]
  • (4S,5R)-2-Oxo-1,5-diphenyl-imidazolidine-4-carboxylic acid [ No CAS ]
  • (4S,5R)-2-Oxo-1,5-diphenyl-imidazolidine-4-carboxylic acid amide [ No CAS ]
  • 76
  • [ 538-51-2 ]
  • [ 25761-72-2 ]
  • N,N-Diallyl-2-phenyl-2-phenylamino-acetamide [ No CAS ]
  • 77
  • [ 694-53-1 ]
  • [ 538-51-2 ]
  • Benzyl-phenyl-phenylsilanyl-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% With hydrogen In toluene at 90℃; for 120h;
With [CpFe(IMes)(CO2)]I at 30℃; for 30h; Inert atmosphere; Neat (no solvent); Irradiation;
With C12H20NSi(1-)*K(1+)*C4H8O In benzene-d6 at 25℃; for 0.0833333h; Glovebox; Inert atmosphere;
  • 78
  • [ 538-51-2 ]
  • [ 93-98-1 ]
  • [ 607-00-1 ]
  • [ 100-52-7 ]
  • 79
  • [ 24850-33-7 ]
  • [ 538-51-2 ]
  • [ 66489-79-0 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: allyltributylstanane With hafnium tetrachloride In EtCN at -40℃; for 2h; Inert atmosphere; Stage #2: benzylidene phenylamine In EtCN at -40℃; for 2h; Inert atmosphere;
96% With zirconium triflate In acetonitrile Ambient temperature;
92% Stage #1: allyltributylstanane With tantalum pentachloride In dichloromethane at -78℃; for 0.5h; Stage #2: benzylidene phenylamine In dichloromethane at -78℃; for 2h;
92% Stage #1: benzylidene phenylamine With MgI2*(OEt2)n In dichloromethane at 20℃; for 0.166667h; Stage #2: allyltributylstanane In dichloromethane at 20℃;
In dichloromethane at 20℃; for 2h;

  • 80
  • [ 39163-39-8 ]
  • [ 538-51-2 ]
  • [ 212691-36-6 ]
YieldReaction ConditionsOperation in experiment
0.48 g With benzaldehyde In diethyl ether for 168h;
  • 81
  • [ 51419-59-1 ]
  • [ 538-51-2 ]
  • (3S,4R)-2-Cyclohexyl-3-phenyl-4-p-tolyl-[1,2]thiazetidine 1,1-dioxide [ No CAS ]
  • (3R,4R)-2-Cyclohexyl-3-phenyl-4-p-tolyl-[1,2]thiazetidine 1,1-dioxide [ No CAS ]
  • 82
  • [ 120-72-9 ]
  • [ 538-51-2 ]
  • [ 35173-74-1 ]
YieldReaction ConditionsOperation in experiment
97% With zinc perchlorate; 1,3-bis[5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-ylmethyleneamino]thiourea In dichloromethane at 20℃; for 10h; Typical procedure for the synthesis of bis(indolyl)alkanes General procedure: A mixture of ligand L3 (0.005g, 0.01 mmol) and Zn(ClO4)2·6H2O (0.004 g, 0.01 mmol) in CH2Cl2 (2 mL) was stirred at room temperature for 0.5 h. Then, indole (0.023g, 0.2mmol) and imine (0.018g, 0.1 mmol) were added. After the reaction was completed as determined by TLC, the crude mixture was purified by column chromatography on silica gel (ethyl acetate/petroleum ether 1:20-1:10) to afford the desired pure product 3a in 97% yield.
87% With N-benzyl-N,N,N-triethylammonium chloride In water for 0.0416667h; Microwave irradiation; Green chemistry;
78% With silica gel; iron(III) chloride for 0.075h; microwave irradiation;
75% With indium(III) chloride In acetonitrile at 20℃; for 4h;
71% With nano n-propylsulfonated γ-Fe2O3 In neat (no solvent) at 80℃; for 0.333333h; Green chemistry;
7.5% With indium(III) chloride; methyl magnesium iodide In acetonitrile for 20h; Ambient temperature;
With trityl tetrafluoroborate In dichloromethane at -78 - 0℃; for 14h; Inert atmosphere;

  • 83
  • [ 72707-66-5 ]
  • [ 538-51-2 ]
  • [ 98351-65-6 ]
  • 84
  • [ 538-51-2 ]
  • [ 100-52-7 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride; water In diethyl ether; toluene at 20℃; for 2h; Inert atmosphere;
98% With hexaaquairon(III) perchlorate for 2h;
98% With tert.-butylhydroperoxide In toluene at 110℃; for 1.25h;
98 % Spectr. With tetrabutylammonium Oxone In acetonitrile at 20℃; for 10h;

  • 85
  • [ 95-89-6 ]
  • [ 538-51-2 ]
  • N-phenyl-N-[1-phenyl-(3,6-dimethylpyrazyl)]methylamine [ No CAS ]
Same Skeleton Products
Historical Records